Category: isoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.26947-41-1,3-Isoquinolinecarbonitrile,as a common compound, the synthetic route is as follows.,26947-41-1

Preparation 152 N -Hydroxy-3-isoquinolinecarboximidamide The title compound was obtained as a white solid from 3-cyanoisoquinoline using a similar method to that described in Preparation 110. 1H NMR (400 MHz, D6-DMSO) 5.93 (s, 2H), 7.67 (dd, 1H), 7.78 (dd, 1H), 8.03 (d, 1H), 8.14 (d, 1H), 8.29 (s, 1H), 9.33 (s, 1H), 9.78 (s, 1H).

The synthetic route of 26947-41-1 has been constantly updated, and we look forward to future research findings.

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.26947-41-1,3-Isoquinolinecarbonitrile,as a common compound, the synthetic route is as follows.,26947-41-1

Example 230 4-Amino-6-chloro-2-(1-(3-isoquinolyl)ethyl)thio-pyrimidine (Cpd #230) Isoquinoline-3-carbonitrile (1.76 g, 11.4 mmole) is dissolved in 10 ml tetrahydrofuran in an oven dried 100 ml two neck round bottom flask under nitrogen. The solution is cooled to 0¡ã C., is diluted with 5 ml diethyl ether, and is treated with methyl magnesium bromide in ether (5.7 ml, 17.1 mmole). The reaction is warmed to reflux for one hour, is cooled to 0¡ã C., and is quenched with 15 ml 6 M hydrochloric acid. The reaction mixture is warmed to 50¡ã C. for one hour, is cooled, and is poured into 75 ml 2N sodium hydroxide. The mixture is extracted with 3*50 ml ethyl acetate and the combined organics are dried over potassium carbonate. The dried organics are concentrated in vacuo to a crude orange solid. The crude material is chromatographed over 60 g silica gel (230-400 mesh), eluding with 20percent acetone/hexane, while collecting 22 ml fractions. Fractions 7-11 are combined and concentrated to provide 1.7 g (87percent) of 3-acetyl-isoquinoline. H-NMR (CDCl3, TMS): delta 2.83 (s,3), 7.70-7.78 (m, 2), 7.97-8.06 (m, 2), 8.47 (s,1), 9.28 (s,1) ppm. 13 C-NMR (CDCl3): delta 26.6; 120.2; 127.6; 128.6; 129.4; 130.1; 131.0; 135.5; 124.7; 151.9; 200.3 ppm. TLC (silica gel-60, F-254): Rf =0.37, 20percent acetone/hexane. Melting Point: 90-91¡ã C. Infrared (nu max, mineral oil): 2925, 1689, 1418, 1386, 1220, 944, 764 cm-1. Mass Spectrum, [M/Z](relative intensity): [171](88). Analysis: Calculated for C11 H9 N1 O1: C, 77.17; H,5.30; N,8.18. Found: C, 76.98; H,5.41; N,8.29

The synthetic route of 26947-41-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pharmacia & Upjohn Company; US6043248; (2000); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

23687-25-4, Isoquinolin-4-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,23687-25-4

In a single-necked round-bottomed flask isoquinoline-4-amine (1 .50 g, 10.4 mmol) and 4-methoxybenzenesulfonyl chloride (2.47 g, 1 1.96 mmol) were dissolved in anhydrous pyridine (18 ml.) and stirred at room temperature overnight. Upon completion of the reaction determined by TLC, the reaction was diluted with water (50 ml.) and extracted with EtOAc (25 ml_). The layers were separated, and the aqueous layer was extracted with EtOAc (2 c 25 ml_). The combined organics were washed with water (50 ml_), brine (2 c 50 ml_), dried over Na2S04, and concentrated under reduced pressure to a brown oil. Toluene (50 ml.) was added to the oil and removed under reduced pressure to yield an orange solid. The crude product was purified by recrystallization from toluene to yield 2.50 grams (77% yield) of (13) as an orange solid.

The synthetic route of 23687-25-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; MOORE, Terry; LAZZARA, Phillip; DAVID, Brian; RICHARDSON, Benjamin; JAIN, Atul, D.; (87 pag.)WO2019/195348; (2019); 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.23687-25-4,Isoquinolin-4-amine,as a common compound, the synthetic route is as follows.,23687-25-4

To a stirring solution of isoquinolin-4-amine (15 g, 104.04 mmol) in HCl (150 mL, 5 mol/L) at 0 C. was added a solution of sodium nitrite (10.77 g, 156.06 mmol) in water (15 mL) at below 0 C. The reaction mixture was stirred at 0 C. for 30 min and a solution of SnCl2.2H2O (58.69 g, 260.10 mmol) dissolved in HCl (27 mL, 12 mol/L) was added dropwise. The mixture was stirred at room temperature for 12 h. The mixture was adjusted to pH 12-14 with 20% aqueous sodium hydroxide. The mixture was extracted with CH2Cl2 (1000 mL*3). The organic layer was dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to afford crude 180a (15.8 g, 95.4% yield) as a brown solid, used directly for the next step.

The synthetic route of 23687-25-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

23687-25-4, Isoquinolin-4-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,23687-25-4

General procedure: To the mixture of 7 (500 mg, 2.0 mmol) and 5-aminoisoquinoline (651 mg, 4.52 mmol) was added p-toluenesulfonic acid monohydrate (50 mg, 0.26 mmol), and the resultant mixture was stirred at 160 C for 24 h. After cooling at room temperature, the mixture was purified using column chromatography on silica gel (CHCl3/MeOH = 98/2) to give crude 15 as a brown solid. The solid was recrystallized from EtOAc to give 15 (300 mg, 40%) as a colorless powder.

The synthetic route of 23687-25-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sugane, Takashi; Tobe, Takahiko; Hamaguchi, Wataru; Shimada, Itsuro; Maeno, Kyoichi; Miyata, Junji; Suzuki, Takeshi; Kimizuka, Tetsuya; Morita, Takuma; Sakamoto, Shuichi; Tsukamoto, Shin-Ichi; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 34 – 41;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

23687-25-4, Isoquinolin-4-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,23687-25-4

Intermediate 87 (1.27 g) was dissolved in 1 N aqueous hydrochloric acid (36 ml) and added dropwise with an aqueous solution (36 ml) of sodium nitrite (1.21 g, Wako Pure Chemical Industries) with ice cooling. The obtained suspension was added dropwise to a solution of copper(I) chloride (1.83 g, Wako Pure Chemical Industries) in 1 N aqueous hydrochloric acid (20 ml) with ice cooling, then warmed to room temperature and stirred for 15 hours. The reaction mixture was added with 28% aqueous ammonia (50 ml) and extracted twice with ethyl acetate (150 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (433 mg).

The synthetic route of 23687-25-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Yamada, Rintaro; Seto, Minoru; US2005/20623; (2005); 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.23687-25-4,Isoquinolin-4-amine,as a common compound, the synthetic route is as follows.,23687-25-4

To a solution of isoquinolin-4-amine (1.00 g, 6.94 mmol) in pyridine (7 mL) at 25 C under nitrogen, was added benzoic anhydride (1.57 g, 6.94 mmol) in pyridine (1.5 mL). The resulting solution was heated at 100 C for 4 h, then cooled to 25C and quenched using saturated solution of NaHCO3 (5 mL). Crude product was extracted with CHCl3 (5×10 mL). Combined organic phase was washed with water (2×15 mL) and brine (15 mL), then dried over Na2SO4, filtered, and concentrated under reduced pressure to yield the title compound as a purple-red solid (1.66 g, 6.70 mmol, 97% yield) that was used without further purification.

The synthetic route of 23687-25-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MARINEAU, Jason, J.; ZAHLER, Robert; CIBLAT, Stephane; WINTER, Dana, K.; KABRO, Anzhelika; ROY, Stephanie; SCHMIDT, Darby; CHUAQUI, Claudio; MALOJCIC, Goran; PIRAS, Henri; WHITMORE, Kenneth, Matthew; LUND, Kate-Iyn; SINKO, Bill; SPROTT, Kevin; (418 pag.)WO2018/13867; (2018); 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.1532-97-4,4-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

To a solution of n-butyl lithium (133 mL, 332.5 mmol, 2.5 M in THF) in 760 mL THF was added a solution of 4-bromoisoquinoline 24a (20 g, 96.6 mmol) in 144 mL THF dropwise at -65¡ã C. and the resulting mixture was stirred at this temperature for another 30 mm after the completion of addition. A solution of N-fluorobenzenesulfonimide (66.68 g, 211.7 mmol) in 216 mL THF was added at -65¡ã C. in 1 h dropwisely. After being stirred for another 1 h at this temperature, the reaction mixture was warmed to room temperature slowly with stirring, after the reaction is over, 300 mL saturated aq. NH4Cl was added slowly, extracted with EtOAc (300 mL*3). The combined organic layers were washed with 300 mL brine, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography (0-100percent EtOAc/PE) to give 4-fluoroisoquinoline 24b (8.5 g, red oil, yield: 60percent).

1532-97-4 4-Bromoisoquinoline 73743, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; MEDSHINE DISCOVERY INC.; WU, Lingyun; YAO, Yuanshan; CHEN, Zhaoguo; CHEN, Shuhui; (69 pag.)US2017/37050; (2017); 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.7651-81-2,Isoquinolin-3(2H)-one,as a common compound, the synthetic route is as follows.

Example 300A 5-nitro-3-isoquinolinol 3-Hydroxyisoquinoline (1.09 g, 7.53 mmol) in concentrated H2SO4 (20 mL) at 0 C. was treated with NaNO3 (0.71 g, 8.34 mmol) in concentrated H2SO4 (5 mL) dropwise over 15 minutes. After stirring for 90 minutes, the mixture was allowed to warm to room temperature, stir for 2 hours, poured over an ice-NH4Cl mixture, and the pH was adjusted to 7-8 with 50% NaOH solution. The mixture was filtered and the filter cake dried to provide the title compound. Structure analysis determined a 2:1 mixture of the 5-nitro and 7-nitro isomers which were not separated. MS (ESI+) m/z 191 (M+H)+; MS (ESI-) m/z 189 (M-H)-; 1H NMR (DMSO, 300 MHz) delta 4.60 (s, 1H), 7.48 (t, J 8.0, 1H), 7.57 (s, 1H), 8.42 (d, J 8.0, 1H), 8.57 (d, J 7.7, 1H), 9.19 (s, 1H).

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Reference£º
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2004/157849; (2004); 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.34784-05-9,6-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

6-Bromoisoquinoline (8, 469 mg, 2.25 mmol), potassium trifluoro(vinyl)borate (755 mg, 5.64 mmol), Cs2CO3 (2.20 g, 6.76 mmol) and dichloro[1,1?-bis(di-tert-butylphosphino)ferrocene]palladium(II) (30mg, 0.05 mmol) were suspended in THF (9 mL) and H2O (1 mL). N2 was bubbled through the slurry for 5 min, which was then sealed into a microwave tube. The reaction mixture was heated to 100 C for 1 h in a microwave reactor and cooled to r.t. The mixture was filtered; the filtrate was diluted with CH2Cl2 (10 mL) and washed sequentially with H2O (10 mL) and sat. brine (10 mL). The organic layer was dried (MgSO4), filtered and evaporated to give a brown oil. The crude productwas purified by flash silica gel chromatography (eluent: gradient 5 to30% EtOAc in heptane). Pure fractions were evaporated to dryness to afford 6-vinylisoquinoline (282 mg, 81%) as a pale yellow liquid.1H NMR (400 MHz, DMSO-d6): delta = 9.28 (s, 1 H), 8.50 (d, J = 5.7 Hz, 1H), 8.10 (d, J = 8.5 Hz, 1 H), 7.95 (s, 1 H), 7.92 (dd, J = 8.5, 1.7 Hz, 1 H),7.80 (d, J = 5.7 Hz, 1 H), 6.96 (dd, J = 17.7, 11.2 Hz, 1 H), 6.12 (d, J = 17.7Hz, 1 H), 5.51 (d, J = 11.2 Hz, 1 H).MS (ES+): m/z = 156 [M + H]+.

The synthetic route of 34784-05-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Pearson, Stuart E.; Fillery, Shaun M.; Goldberg, Kristin; Demeritt, Julie E.; Eden, Jonathan; Finlayson, Jonathan; Patel, Anil; Synthesis; vol. 50; 24; (2018); p. 4963 – 4981;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem