Category: 1198-30-7

1198-30-7, 1-Isoquinolinecarbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1198-30-7, A solution of isoquinoline-1-carbonitrile (Intemediate H1) (commercially available from Aldrich) (4.40 g, 28.5 mmol) in THF at 0 C. was treated with methylmagnesium bromide (20 mL, of a 3M soln in ether) for 3 h. (see procedure found in Vacher, B. et al J. Med. Chem. 1998 41, 5070; incorporated herein by reference). The mixture was quenched with a sat. solution of NH4Cl and stirred for 3 h at rt. The aqueous layer was basified with NaOH and extracted with ethyl acetate. The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by chromatography on silica gel with 10% ethyl acetate: hexane to give 1-isoquinolin-1-yl-ethanone (Intermediate H2) 3.65g (75%). A mixture of 4-iodo-1-tritylimidazole (commercially available) (15.5 g, 35.4 mmol) in dichloromethane (80 mL) at 20 C. was treated with ethyl magnesium bromide (12.0 mL, 36 mmol, 3M in ether) and allowed to react for 1 h. A solution of 1-isoquinolin-1-yl-ethanone (Intermediate H2) (3.65 g, 21.3 mmol) in dichloromethane (20 mL) was added via addition funnel at 20 C. and stirred for 16 h. The mixture was quenched with sat. ammonium chloride (100 mL) and diluted with dichloromethane. The residue was isolated in an aqueous workup. The product was extracted with CH2Cl2 and purified by chromatography on silica gel with 5% NH3-MeOH: CH2Cl2 to give 1-isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H3) as a solid. 1-Isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H3) was subjected to TFA: trifluoroacetic acid, Pd/C under hydrogen similar to the catalytic reduction procedure of Method D to remove the trityl group and produced 1-1H-imidazol-4-yl)-isoquinolin-1-yl ethanol (Intermediate H4). 1-1H-Imidazol-4-yl)-isoquinolin-1-yl ethanol (Intermediate H4). (21 mmol) in dichloromethane (100 mL) was treated with triethylamine (24.0 mL, 172 mmol) at 0 C. Methanesulfonyl chloride (6.1 mL, 75 mmol) was added via syringe and the mixture was stirred for 2 h. The mixture was subjected to an aqueous work-up. The crude material was purified by chromatography on silica gel with 20% EtOAc: hexane to 5% NH3-MeOH: dichloromethane to give 1-[1-(1-methanesulfonyl-1H-imidazol-4-yl)-vinyl]-isoquinoline (Intermediate H5) 3 g. 1-[1-(1-Methanesulfonyl-1H-imidazol-4-yl)-vinyl]-isoquinoline (Intermediate H5) was subjected to the catalytic reduction procedure found in Method D to produce 1-[1-(1-methanesulfonyl-1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H6). Methanesulfonyl-1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H6) in ethanol and 2M HCl was heated at reflux for 18 h. The mixture was cooled to rt and basified with NaOH solid. The aqueous layer was extracted with isopropanol:chloroform (3:1). The organic fractions were dried over MgSO4, filtered and concentrated onto silica gel. The product, 1-[1-(1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H7) was eluted from a column of silica gel with 3 to 5% NH3-MeOH: CH2Cl2. 1-[1-(1H-Imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H7) was subjected to the appropriate process steps in Method A to produce 4-(1-isoquinolin-1-yl-ethyl)-1,3-dihydro-imidazole-2-thione (Compound 13) 1H NMR (300 MHz, DMSO-d6): delta11.9 (s, 1H), 11.6 (s, 1H), 8.42 (dd, J=5.4, 2.7 Hz, 1H), 8.31 (d, J=8.1 Hz, 1H), 7.96 (d, J=8.1 Hz, 1H), 7.78-7.64 (m, 3H), 6.40 (s, 1H), 5.0 (q, J=6.9 Hz, 1H), 1.59 (d, J=6.9 Hz, 3H).

1198-30-7 1-Isoquinolinecarbonitrile 306057, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Allergan, Inc.; US2006/69143; (2006); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

1198-30-7, 1-Isoquinolinecarbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1198-30-7, EXAMPLE X Preparation of N-[(1,2,3,4-Tetrahydro-2-methyl-1-isoquinolyl)methyl]-N-benzylpropionamide oxalate (TR-3389) Title Compound I, in which R=CH3 R’=H; X=H; A=CH; pY=C2 H2 O4 and q=0 and n=1 was prepared as follows: 1-Cyanoisoquinoline (15.4 g; 0.1 mole) was stirred and heated at reflux for 2.5 hours in 900 ml. of a 1:1 formic acid water solution with 30 g of Raney nickel alloy. The reaction was filtered and the filtrate made basic with 20% NaOH. The resulting suspension was extracted with dichloromethane whereupon the organic layer was separated, dried over MgSO4 and evaporated in vacuo to leave 9.5 g of a green oil. The crude oil was chromatographed through a silica gel column with ethyl acetate; evaporation of the ethyl acetate in vacuo left 7.5 g (40% theory) of 1-formamidoisoquinoline as a yellow oil. This compound was converted to the methiodide salt and reduced catalytically as in Example I to give a 50% yield of 1-formamidomethyl-2-methyl-1,2,3,4-tetrahydroisoquinoline as a yellow oil, 4 g (0.02 mole) of which was refluxed for 60 minutes in 10 ml of concentrated HCl.

1198-30-7 1-Isoquinolinecarbonitrile 306057, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Miles Laboratories, Inc.; US4232160; (1980); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1198-30-7,1-Isoquinolinecarbonitrile,as a common compound, the synthetic route is as follows.

1198-30-7, Preparation 149 N’-Hydroxy-1-isoquinolinecarboximidamide The title compound was obtained as a white solid from 1-cyanoisoquinoline using a similar method to that described in Preparation 110. 1H NMR (300 MHz, D6-DMSO) delta 5.94 (s, 2H), 7.67 (dd, 1H), 7.78 (dd, 1H), 7.86 (d, 1H), 7.99 (d, 1H), 8.52 (d, 1H), 9.07 (d, 1H), 10.11 (s, 1H).

As the paragraph descriping shows that 1198-30-7 is playing an increasingly important role.

Reference£º
Patent; Bailey, Simon; Fish, Paul Vincent; James, Kim; Whitlock, Gavin Alistar; US2003/69291; (2003); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1198-30-7,1-Isoquinolinecarbonitrile,as a common compound, the synthetic route is as follows.

1198-30-7, Example B3 (4-Butylphenyl) (1-isoquinolyl)ketone 1-Bromo-4-butylbenzene (2.29 ml, 13 mmol) and a catalytic amount of 1,2-dibromoethane as an initiator were added to a mixedsolution of magnesium (338 mg, 14 mmol) and tetrahydrofuran (6.5 ml) under nitrogen atmosphere, and this mixture was stirred under reflux for 10 minutes. The mixture was cooled to 0C, a solution of 1-isoquinolinecarbonitrile (1.0 g, 6.5 mmol) in tetrahydrofuran was added, and this mixture was stirred at room temperature for 1 hour, then at 70C for 3 hours. Thereafter, the mixture was cooled again to 0C, concentrated hydrochloric acid (2.6 ml) and methanol (11 ml) were added, and this mixture was heated under reflux for 2 hours. After the mixture was concentrated, the residue was dissolved in 5 N sodium hydroxide and toluene, and was filtered through celite. The toluene layer of the filtrate was separated, washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.7 g). 1H-NMR(CDCl3) delta (ppm):0.93(3H, t), 1.32-1.43(2H, m), 1.58-1.66(2H, m), 2.68(2H, t), 7.28(2H, d), 7.61(1H, td), 7.74(1H, td), 7.80(1H, d), 7.87(2H, d), 7.92(1H, d), 8.20(1H, d), 8.60(1H, d)

The synthetic route of 1198-30-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eisai Co., Ltd.; EP1300464; (2003); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

1198-30-7, 1-Isoquinolinecarbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1198-30-7, Example A13 Synthesis of (4-butylphenyl)(1-isoquinolyl)ketone Under a nitrogen atmosphere, 1-bromo-4-butylbenzene (2.29 ml, 13.0 mmol) was added to a mixed solution of magnesium (338 mg, 13.9 mmol) and tetrahydrofuran (6.5 ml), and as an initiator, catalytic amount of 1,2-dibromoethane was added, and this was stirred under reflux for 10 minutes. The solution was cooled to 0C, a tetrahydrofuran solution of 1-isoquinolinecarbonitrile (1.0g, 6.49 mmol) was added, and was stirred for another 1 hour at room temperature, and at 70C for 3 hours. Subsequently, the solution was cooled again to 0C, concentrated hydrochloric acid (2.56 ml) and methanol (11 ml) were added, and then refluxed for 2 hours. The concentrated residue was dissolved in 5 N sodium hydroxide and toluene, and was filtered through celite. The toluene layer of the filtrate was divided, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give 1.72 g of the title compound. 1H-NMR(CDCl3) delta (ppm):0.93(3H, t), 1.32-1.43(2H, m), 1.58-1.66(2H, m), 2.68(2H, t), 7.28(2H, d), 7.61(1H, td), 7.74(1H, td), 7.80(1H, d), 7.87(2H, d), 7.92(1H, d), 8.20(1H, d), 8.60(1H, d)

As the paragraph descriping shows that 1198-30-7 is playing an increasingly important role.

Reference£º
Patent; Eisai Co., Ltd.; EP1300464; (2003); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem