Tag: M.W:200-300

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine, is researched, Molecular C12H10N6, CAS is 1671-88-1, about Ruthenium carbonyl complexes of N-heterocyclic molecules. Part 3. Synthesis of ruthenium complexes of the ambidentate ligand 4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole (APT). X-ray crystal structures of two coordination isomers of Ru(CO)2Cl2(APT).Safety of 3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine.

4-Amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole (APT), a poly- and ambidentate ligand, forms 2 bidentate coordination isomers of Ru(CO)2Cl2, which in 1 case is coordinated to a pyridyl ring and an adjacent triazole ring (A), and in the other case to a pyridyl ring and the amino N atom (B). Both isomers of Ru(CO)2Cl2(APT) were crystallog. characterized: A, orange, orthorhombic, space group Pbca, a 15.332(4), b 17.715(4), c 13.083(4) Å, R = 3.26%; B(MeOH), yellow, triclinic, space group P1̅, a 8.712(2), b 9.492(2), c 12.142(2) Å, α 86.03(2), β 82.63(2), γ 74.21(2)°, R = 3.49%. The complexes are formed directly from the reaction of [Ru(CO)2Cl2]n with APT in boiling MeOH. In a similar reaction with Re(CO)5Cl, Re(CO)3Cl(APT) is formed. The Br analog of the Ru complex forms predominantly the yellow isomer (B), while the I analog crystallizes only as the orange isomer (A). Based on NMR data, the Re complex most likely coordinates via the A mode.

《Ruthenium carbonyl complexes of N-heterocyclic molecules. Part 3. Synthesis of ruthenium complexes of the ambidentate ligand 4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole (APT). X-ray crystal structures of two coordination isomers of Ru(CO)2Cl2(APT)》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine)Safety of 3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine.

Reference:
Isoquinoline – Wikipedia,
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Computed Properties of C12H10N6. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine, is researched, Molecular C12H10N6, CAS is 1671-88-1, about Inducing Effect of Additive Agents on Coordination Assembly of Silver(I) Nitrate with 3,5-Bis(2-pyridyl)-4-amino-1,2,4-triazole: Supramolecular Isomerism and Interconversion. Author is Li, Cheng-Peng; Wu, Jing-Min; Du, Miao.

By using different organic acids as additive agents, hydrothermal reactions of AgNO3 with 3,5-bis(2-pyridyl)-4-amino-1,2,4-triazole (2-bpt) gives two conformational polymorphs of [Ag(2-bpt)](NO3) with bimetallocyclic and 1-D helical coordination patterns. Interconversion between the two supramol. isomers can be achieved under proper conditions, which will pass through the same intermediate state.

《Inducing Effect of Additive Agents on Coordination Assembly of Silver(I) Nitrate with 3,5-Bis(2-pyridyl)-4-amino-1,2,4-triazole: Supramolecular Isomerism and Interconversion》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine)Computed Properties of C12H10N6.

Reference:
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Isoquinoline | C9H7N – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Diphenyl-2-pyridylphosphine, is researched, Molecular C17H14NP, CAS is 37943-90-1, about The impact of cyclometalated and phosphine ligands on the luminescence properties of cycloplatinated(II) complexes: photophysical and theoretical investigations, the main research direction is platinum difluorophenylpyridine cyclometalated phosphine DMSO complex preparation photoluminescence.Recommanded Product: Diphenyl-2-pyridylphosphine.

The present work investigates the synthesis and characterization of a series of cycloplatinated(II) complexes, bearing the 2-(2,4-difluorophenyl)pyridine (dfppy) cyclometalated ligand with the general formula of [Pt(dfppy)(Cl)(L)] (A, 1a, 1b; L = DMSO, PPh2py, PPh3). The phosphine-containing dfppy derivatives are photophys. compared with their previously reported ppy (2-phenylpyridine) counterparts. UV-Vis absorption spectra of these complexes were assigned using TD-DFT (time-dependent d. functional theory) calculations It is observed that the wavelengths (low-energy region) used for excitation are related to the mixed 1ILCT/1MLCT/1XLCT electronic transitions. Theor. investigations on the frontier MOs of the T1 states confirmed that these transitions are also kept in the triplet excited states and lead to the emissive states with 3ILCT/3MLCT/3XLCT character. This would be exptl. verified by the appearance of the structured emission bands and the 3ILCT being mainly present in the emissive state. However, the dfppy derivatives show dual emission bands (high energy as a structured emission band and low energy as an unstructured emission band) in the solid state, which are not observed in the ppy analogs. The dfppy complexes exhibit spectral blue shifts and have higher quantum yield values compared with the ppy analogs. In this regard, the complexes with PPh2py show stronger emissions than those containing PPh3.

《The impact of cyclometalated and phosphine ligands on the luminescence properties of cycloplatinated(II) complexes: photophysical and theoretical investigations》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(Diphenyl-2-pyridylphosphine)Recommanded Product: Diphenyl-2-pyridylphosphine.

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Isoquinoline – Wikipedia,
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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Diphenyl-2-pyridylphosphine(SMILESS: P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=NC=CC=C3,cas:37943-90-1) is researched.Application In Synthesis of (1S,2S)-2-Aminocyclohexanol. The article 《Phosphination of Phenol Derivatives and Applications to Divergent Synthesis of Phosphine Ligands》 in relation to this compound, is published in Organic Letters. Let’s take a look at the latest research on this compound (cas:37943-90-1).

The authors describe a general and efficient protocol for the synthesis of organophosphine compounds from phenols and phosphines (R2PH) via a metal-free C-O bond cleavage and C-P bond formation process. This approach exhibits broad substrate scope and excellent functional group tolerance. The synthetic utilities of this protocol were demonstrated by the synthesis of chiral ligands via the various transformations of cyano groups and their applications in asym. catalysis.

《Phosphination of Phenol Derivatives and Applications to Divergent Synthesis of Phosphine Ligands》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(Diphenyl-2-pyridylphosphine)Synthetic Route of C17H14NP.

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called A porous metal-organic cage constructed from dirhodium paddle-wheels: synthesis, structure and catalysis, published in 2015, which mentions a compound: 67929-86-6, mainly applied to rhodium phenylenebisethynediyldibenzoate cage complex preparation structure cycloamination catalyst; crystal structure rhodium phenylenebisethynediyldibenzoate tetranuclear cage complex, Product Details of 67929-86-6.

Self-assembly of dirhodium(II) tetraacetate (Rh2(OAc)4) with a dicarboxylic acid 3,3′-(1,3-phenylenebis(ethyne-2,1-diyl))dibenzoic acid (H2pbeddb) gives rise to a metal-organic cage (MOC) containing Rh-Rh bonds with the formula of [Rh4(pbeddb)4(H2O)2(DMA)2] (MOC-Rh-1). Single-crystal x-ray diffraction anal. reveals that MOC-Rh-1 shows a lantern-type cage structure, in which a pair of Rh2(CO2)4 paddlewheels is linked by four diacid ligands. The dimensions of the inner cavity of MOC-Rh-1 are 9.5 × 14.8 Å2 (atom-to-atom distances across opposite metal and Ph groups of pbeddb2-). In the solid phase, the cages are aligned by π-π stacking to form one-dimensional channels (9.5 × 11.1 Å2) through cage windows. Therefore, the crystalline samples of MOC-Rh-1 are porous with the inner and outer cavities of the cages accessible under the heterogeneous condition. MOC-Rh-1 was fully characterized by EA, TGA, PXRD, IR, UV-visible and XPS measurements. The catalytic tests disclose that activated MOC-Rh-1 is effective in the intramol. C-H amination of vinyl, dienyl and biaryl azides, giving indoles, pyrroles and carbazoles, resp., and the porous catalyst can be recycled easily and used for at least nine runs without significant loss of activity. In the nine runs, the conversions were at 93-99%, whereas in the tenth run, the conversion was reduced to 78%.

《A porous metal-organic cage constructed from dirhodium paddle-wheels: synthesis, structure and catalysis》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(Methyl 5-methoxyindole-2-carboxylate)Product Details of 67929-86-6.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis, structure and magnetic properties of mono-, dinuclear and polymeric compounds of transition metals with 4-amino-3,5-di-2-pyridyl-4H-1,2,4-triazole》. Authors are Martin-Ramos, Pablo; Silva, Manuela Ramos; de A. e Silva, Joana; Martins, Nuno D.; Yuste-Vivas, Consuelo; Pereira da Silva, Pedro S.; Sobral, Abilio J. F. N.; Pereira, Laura C. J..The article about the compound:3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-aminecas:1671-88-1,SMILESS:NN1C(C2=NC=CC=C2)=NN=C1C3=NC=CC=C3).Synthetic Route of C12H10N6. Through the article, more information about this compound (cas:1671-88-1) is conveyed.

Five new complexes were obtained from solution of transition metal salts (M=Co(II), Cu(II)) with 4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole (abpt) in different molar ratios, [CuCl2(L)2]·H2O (1, 2), [Cu(PhCOO)2(L)2]·4PhCOOH (3), {[CuCl(L)]2(CuCl2)·4H2O}n (4), [Co(H2O)Cl(L)]2·Cl2·4H2O (5). X-ray structural elucidation revealed low-dimensional compounds with the metal ions assembled in monomers, dimers or chains. Two similar polymorphs were obtained for the monomer synthesized from Cu(II) chloride. Temperature-dependent magnetic susceptibility measurements were conducted for the non-monomeric compounds, and efficient super-exchange interaction was found for the mostly planar dinuclear Co(II) complex.

《Synthesis, structure and magnetic properties of mono-, dinuclear and polymeric compounds of transition metals with 4-amino-3,5-di-2-pyridyl-4H-1,2,4-triazole》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine)Synthetic Route of C12H10N6.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kitchen, Jonathan A.; Noble, Andy; Brandt, Carsten D.; Moubaraki, Boujemaa; Murray, Keith S.; Brooker, Sally published the article 《High and Low Spin Mononuclear and Dinuclear Iron(II) Complexes of 4-Amino and 4-Pyrrolyl-3,5-di(2-pyridyl)-4H-1,2,4-triazoles》. Keywords: iron aminopyridyltriazole pyrrolylpyridyltriazole chloro mononuclear dinuclear preparation magnetic property; crystal structure iron aminopyridyltriazole pyrrolylpyridyltriazole chloro mononuclear dinuclear.They researched the compound: 3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine( cas:1671-88-1 ).SDS of cas: 1671-88-1. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:1671-88-1) here.

The 1st dinuclear iron(II) complexes of any 4-substituted 3,5-di(2-pyridyl)-4H-1,2,4-triazole ligands, [FeII2(adpt)2(H2O)1.5(CH3CN)2.5](BF4)4 and [FeII2(pldpt)2(H2O)2(CH3CN)2](BF4)4, are presented [where adpt is 4-amino-3,5-di(2-pyridyl)-4H-1,2,4-triazole and pldpt is 4-pyrrolyl-3,5-di(2-pyridyl)-4H-1,2,4-triazole]. Both dinuclear complexes feature doubly triazole bridged iron(II) centers that are [high spin-high spin] at all temperatures, 4-300 K, and to exhibit weak antiferromagnetic coupling. In the analogous monometallic complexes, [FeII(Rdpt)2(X)2]n+, the spin state of the iron(II) center was controlled by appropriate selection of the axial ligands X. Specifically, both of the chloride complexes, [FeII(adpt)2(Cl)2]·2MeOH and [FeII(pldpt)2(Cl)2]·2MeOH·H2O, are high spin whereas the pyridine adduct [FeII(adpt)2(py)2](BF4)2 was low spin. Attempts to prepare [FeII(pldpt)2(py)2](BF4)2 and the dinuclear analogs [FeII2(Rdpt)2(py)4](BF4)4 failed, illustrating the significant challenges faced in attempts to develop control over the nature of the product obtained from reactions of iron(II) and these bis-bidentate ligands.

《High and Low Spin Mononuclear and Dinuclear Iron(II) Complexes of 4-Amino and 4-Pyrrolyl-3,5-di(2-pyridyl)-4H-1,2,4-triazoles》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine)SDS of cas: 1671-88-1.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Methyl 5-methoxyindole-2-carboxylate(SMILESS: O=C(C(N1)=CC2=C1C=CC(OC)=C2)OC,cas:67929-86-6) is researched.HPLC of Formula: 16400-32-1. The article 《Efficient mononitration of indolic compounds with nitric acid impregnated on silica gel》 in relation to this compound, is published in Heterocycles. Let’s take a look at the latest research on this compound (cas:67929-86-6).

The methoxyindoles I (R = H, R1 = SO2Ph, MeO position = 4-7; R = CO2Me, R1 = H, MeO position = 4-7) were mononitrated with nitric acid adsorbed on silica gel under mild conditions to give mononitroindoles in good chem. yields.

This compound(Methyl 5-methoxyindole-2-carboxylate)Application of 67929-86-6 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Three zinc(II) and cadmium(II) complexes containing 4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole and polynitrile ligands: synthesis, molecular and supramolecular structures, and photoluminescence properties, published in 2017-09-01, which mentions a compound: 1671-88-1, Name is 3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine, Molecular C12H10N6, Reference of 3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine.

Three photoluminescent complexes containing either ZnII or CdII have been synthesized and their structures determined Bis[4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-κ2N1,N5]bis(dicyanamido-κN1)zinc(II), [Zn(C12H10N6)2(C2N3)2], (I), bis[4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-κ2N1,N5]bis(dicyanamido-κN1)cadmium(II), [Cd(C12H10N6)2(C2N3)2], (II), and bis[4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-κ2N1,N5]bis(tricyanomethanido-κN1)cadmium(II), [Cd(C12H10N6)2(C4N3)2], (III), all crystallize in the space group P [inline formula omitted] , with the metal centers lying on centers of inversion, but neither analogs (I) and (II) nor CdII complexes (II) and (III) are isomorphous. A combination of N-H···N and C-H···N hydrogen bonds and π-π stacking interactions generates three-dimensional framework structures in (I) and (II), and a sheet structure in (III). The photoluminescence spectra of (I)-(III) indicate that the energies of the π-π* transitions in the coordinated triazole ligand are modified by minor changes of the ligand geometry associated with coordination to the metal centers.

Different reactions of this compound(3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine)Reference of 3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine require different conditions, so the reaction conditions are very important.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Hydrogenation of isoxazoles with Raney nickel》. Authors are D’Alcontres, G. Stagno.The article about the compound:1,5-Diphenyl-1H-pyrazole-3-carboxylic acidcas:13599-22-9,SMILESS:OC(=O)C1=NN(C(=C1)C1=CC=CC=C1)C1=CC=CC=C1).COA of Formula: C16H12N2O2. Through the article, more information about this compound (cas:13599-22-9) is conveyed.

The object of the work was to ascertain whether 4-isoxazolines are capable of existence and whether it is possible to prepare them by hydrogenation of isoxazole (I) and its derivatives by a reaction analogous to that of the formation of pyrazolines from pyrazoles [Ber. 26, 100(1893)]. Under the conditions used by Claisen with I derivatives, the ring is opened with formation of the isomeric imino ketones, NH:CRCHR’COR” (IA) (cf. Ber. 24, 3912(1891)), so a less drastic method had first of all to be derived. To this end, Raney Ni (II) in neutral alc. or aqueous media at room temperature and atm. pressure (according to the nature of the I derivative) was tested as a catalyst. In all cases, hydrogenation progressed smoothly, but in no case was a cyclic isoxazoline isolated, and, on addition of 1 H mol., opening of the nucleus occurred, with formation of IA. The experiments confirm the instability of the cyclic system of 4-isoxazolines, which are probably incapable of existence, or at least it is probably impossible to synthesize them by hydrogenation of the I nucleus (Panizzi, C.A. 40, 7190.1). I (2 g.) in 20 cc. alc. and 1.5 g. II, hydrogenated and filtered, give a liquid which has the odor of NH3, is alk. to litmus, gives a blood-red color with FeCl3, and reduces warm NH3AgNO3. This reaction liquid (15 cc., i.e., 0.5 the total) and p-O2NC6H4NHNH2 (III), allowed to stand 1 hr., filtered, and the residue (1.54 g.) purified by dilute EtOH and animal charcoal, yields 1-(p-nitrophenyl)pyrazole (IV), m. 168.5-9°, insoluble in aqueous alkalies and gives no color with them. The other half of the reaction liquor gives no precipitate with H2NCONHNH2.HCl and NaOAc, even after several days. 1-Phenylpyrazole (2 g.), poured very slowly into ice-cold fuming HNO3 (much heat is evolved), allowed to stand, poured into ice water, and the precipitate (3.1 g.) purified by EtOH, yields IV. Dimethylisoxazole (5 g.) in 50 cc. alc. and 2.5 g. II, hydrogenated, filtered, slowly evaporated, and the sirupy residue allowed to stand in vacuo until crystallized, yields MeC(:NH)CH2Ac (V), m. 43° (from EtOH) [cf. Ber. 24, 3915(1881); Bull. soc. chim. 7, 779(1892)]. V (0.5 g.) in dilute AcOH and III in AcOH give a precipitate of 1-(p-nitrophenyl)-3,5-dimethylpyrazole (VI), light yellow, m. 99.5-100° (from dilute EtOH). VI (0.35 g.) in 10 cc. dilute H2SO4, distilled, part of the distillate treated with III, and the precipitate purified by EtOH, yields VI. Another part of the distillate and KOH distilled, and the distillate treated with III, give a p-nitrophenylhydrazone, m. 148.5°. The mother liquor gives the reaction of AcOH. The distillation residue, treated with H2SO4, and made alk., evolves NH3. Diphenylisoxazole (1.5 g.) in 80 cc. alc. and 3 g. II, hydrogenated (with FeCl3 the reaction liquor turns dark green, then red) and evaporated, yields dibenzoylmethaneimide, PhC(:NH)CH2Bz (VII), m. 97° (from alc.), soluble in acids and reprecipitated by aqueous alkali carbonates. VII (0.5 g.) in 20 cc. dilute H2SO4, refluxed 30 min., half of the liquid saturated with (NH4)2SO4, extracted with Et2O, the extract dried, and the residue purified by EtOH, yields the compound C15H12O2, m. 77-8°; FeCl3 turns its alc. solutions violet-red. The other half of the liquid, extracted with Et2O, and the residue treated with concentrated KOH, evolves NH3. VII (0.2 g.) in dilute AcOH and PhHNNH2 (VIII), heated to boiling and allowed to stand, yield 1,3,5-triphenylpyrazole, m. 137-8° (from Et2O) [cf. Ber. 21, 1206(1888); Ann. 308, 252(1889)]. O.N:CMe.CH:CCO2Na (4 g.) in 40 cc. water and 2 g. II, hydrogenated, filtered, and the green filtrate kept in vacuo, leaves a sirupy residue (IX) whose aqueous solutions are alk. to litmus, turn blood-red with FeCl3, and with KOH evolve NH3. Aqueous IX and III give 1-(p-nitrophenyl)-3-methyl-5-pyrazolecarboxylic acid, m. 231° (from EtOH) (cf. Musante and Berretti, C.A. 44, 4905a). VIII (2 cc.), 7 cc. water, 0.3 cc. glacial AcOH, and 0.3 g. IX, heated and allowed to stand yield 1-phenyl-3-methyl-5-carboxypyrazole, m. 189-90° (from hot water), decompose 200-10°, with evolution of CO2 and formation of 1-phenyl-3-methylpyrazole. VIII (1 g.) in 25 cc. dilute H2SO4, boiled, saturated with (NH4)2SO4, extracted with Et2O, and the extract evaporated yields the compound C5H6O4 (IX), m. 98° (from C6H6). IX (0.1 g.) in boiling aqueous KOH evolves Me2CO, and the distillate gives with III a p-nitrophenylhydrazone, yellow, m. 148°. The distillation residue, acidified with AcOH, and aqueous CaCl2 added, precipitates Ca oxalate (X). O.N:C(CO2Na).CH:CMe (3.5 g.) in 40 cc. water and 2 g. II, hydrogenated, and the filtered product evaporated, gives a green sirupy product, which with III yields 1-(p-nitrophenyl)-3-methyl-5-pyrazolecarboxylic acid (XI), m. 231° (from EtOH), turns intense red with FeCl3; with KOH its aqueous solutions evolve NH3; boiling in dilute H2SO4 and extraction with Et2O yields a compound m. 98°. O.N:C(CO2Et).CH:CHMe (5 g.) in 40 cc. alc. and 2 g. II, hydrogenated (the mixture turns brown, is alk., and gives with FeCl3 a cherry-red solution), and the filtered product allowed to evaporate, yields a compound (XII), C7H11O3N, m. 109-10° (from EtOH), soluble in dilute aqueous alkalies; in boiling aqueous KOH it evolves NH3 and Me2CO, and the residue contains X. XII and III in dilute AcOH precipitate a compound which, purified by dilute EtOH and animal charcoal, yields Et 1-(p-nitrophenyl)-3-methyl-5-pyrazolecarboxylate (XIII), yellowish, m. 78-9°. Alc. XIII (0.5 g.) and 0.4 g. KOH in 4 cc. water, refluxed 75 min., evaporated, the residue taken up in water, filtered, the filtrate acidified with HCl, and the precipitate purified by EtOH and animal charcoal, yield XI. O.N:CPh.C(CO2Na):CMe (1.2 g.) in 25 cc. water and 1 g. II, hydrogenated (the product is alk. and turns red with FeCl3), and evaporated, leaves a sirup (XIV), which with HCl evolves CO2. XIV and KOH evolve NH3; distillation (odor of BzMe) and treatment of the distillate with III in AcOH gives p-O2NC6H4NHN:CPhMe. The mother liquor, saturated with (NH4)2SO4, extracted with Et2O, and the extract evaporated, leaves HCO2H. Aqueous XIV and dilute H2SO4 (1:1), allowed to stand until no more CO2 is evolved, saturated with NH3, extracted with Et2O, and the extract evaporated, leave a yellow acidic oil (XV) which reduces NH3-AgNO3. XV, exactly neutralized with dilute NaOH, and aqueous PhNH2.HCl added, yields BzCH2CH:NPh, m. 140-1° (from EtOH) [cf. Ber. 20, 2192(1887)]. O.N:C(CO2Na).CH:CPh (2 g.) in 30 cc. water and 1 g. II, hydrogenated, the reaction liquor (alk. to litmus and turns orange-red with FeCl3) acidified with dilute H2SO4, filtered (the filtrate has the odor of NH3), and the residue purified by C6H6, yield PhC(:NH)CH2COCO2H (XVI), m. 161° (decomposition) (Mumm and Münchmeyer, C.A. 5, 703). XVI (0.48 g.) in dilute AcOH and VIII in AcOH give a precipitate of diphenylpyrazolecarboxylic acid (XVII), m. 185° (from C6H6) [cf. Ber. 20, 2186(1887)]. XVII, heated until no more CO2 is evolved, then at 250°, the yellow oil allowed to solidify in vacuo, dissolved in aqueous HCl, and water added, precipitates a compound, C15H12N2 (XIX), m. 55-6°. XIX in dilute H2SO4, refluxed 1 hr., allowed to stand, filtered, and the residue purified by boiling water, yields a compound, C10H8O4.2H2O (XX), m. 156-8° (decomposition to BzMe); its aqueous solutions are acid to litmus; its solutions in concentrated H2SO4 are purple-red (decolorized by dilution with water). Na salt, precipitates with aqueous FeSO4 a dark blue compound and, fused with resorcinol, gives a dark red product. The mother liquor from XX and aqueous KOH evolve NH3. O.N:CMe.C(CO2Na):CPh (3.1 g.) in 20 cc. water and 1.5 g. II, hydrogenated, the liquid (yellow, alk., and turns intense red with FeCl3), acidified with dilute HCl, evaporated, and the residue purified by boiling EtOH, yield a compound C11H11O3N (XXI), m. 89-90°. XXI in dilute H2SO4, distilled, and the distillate allowed to stand, yields a compound, C10H10O2, m. 60-1°, soluble in aqueous alk. carbonates, with FeCl3 turns Bordeaux red. Treatment of the mother liquor with aqueous KOH yields NH3. XXI in dilute AcOH and VIII in AcOH give 1-(p-nitrophenyl)-3-methyl-5-phenylpyrazole, m. 100-1° (from MeOH) (Reilly, et al., C.A. 26, 452).

Different reactions of this compound(1,5-Diphenyl-1H-pyrazole-3-carboxylic acid)COA of Formula: C16H12N2O2 require different conditions, so the reaction conditions are very important.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem