Category: isoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4721-98-6,6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline,as a common compound, the synthetic route is as follows.

EXAMPLE 6 Preparation of 1-[bis(hydroxymethyl)-methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline To 1 mole (205.3 g) of 1-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline 100 ml of a 30% aqueous formaldehyde solution and then freshly prepared sodium methylate (1 g of sodium+50 ml of methanol) are added. The mixture is then slightly refluxed in 500 ml of methanol for 2 hours. The reaction mixture is evaporated under reduced pressure and the obtained crystalline product is recrystallized from a mixture of acetone and ether. The aimed compound is obtained with the same melting point as the product of Example 1.

4721-98-6, 4721-98-6 6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline 22652, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Richter Gedeon Vegyeszeti Gyar R.T.; US4656179; (1987); A;,
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74417-44-0, 1-(Bromomethyl)isoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,74417-44-0

1-(bromomethyl)isoquinoline (150 mg, 0.675 mmol) was dissolved in chloroform (15 mL) and cooled in water-ice bath m-chloroperoxobenzoic acid (77%, 0.230 g, 1.03 mmol) was added while stirring. The reaction mixture was let to gradually warm up to room temperature and stirred for 24 hours. The solvent was evaporated and the residue was purified by column chromatography on silica in methanol/ethyl acetate mixture. Fractions containing the product were evaporated to give 102 mg of product as pale yellow solid (0.430 mmol, 64 % yield relative to l-(bromomethyl)isoquinoline).’H NMR (CDC13, 25 C, 500 MHz): 5.17 (C//2-arom.. s, 2H); 7.61 ( arom ., ddd,1H,3/HH= 8 Hz,3/HH= 7 Hz,4/HH= 1 Hz); 7.64 (arom., d, 1H,3/HH = 7 Hz); 7.73(arom., ddd, 1H,3/HH = 9 Hz,3/HH = 7 Hz,4/HH = 1 Hz); 7.80-7.83 (arom., m, 1H);7.95 (arom., ddd, 1H,3/HH= 9 Hz,4/HH= 2 Hz,4/HH= 1 Hz); 8.19 (arom., d, 1H,3/HHNMR (CDC13, 25 C, 125 MHz): 5C20.9 (C//2-arom., s); 122.9 (arom., s); 124.0 (arom., s); 127.6 (arom., s); 127.8 (arom., s); 128.6 (arom., s); 128.8 (arom., s); 129.9 (arom., s); 136.9 (arom., s); 143.1 (arom., s).HRMS (ESI) m/z: [(M + H)+] (Ci0H9BrNO) calculated: 237.9862, found: 237.9863

74417-44-0 1-(Bromomethyl)isoquinoline 2776246, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I.; POLASEK, Miloslav; (102 pag.)WO2019/106182; (2019); A1;,
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164148-92-9, tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. 6-(Toluene-4-sulfonylamino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert butyl ester To a mixture of 275 mg (1.10 mmol) of 6-amino-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester, 134 mg (1.33 mmol) of triethylamine in 6 mL of methylene chloride at 00C was added 233 mg (1.2 mmol) of toluenesulfonyl chloride in one portion. The mixture was allowed to warm to room temperature and was stirred overnight. An additional 62 mg (0.61 mmol) of triethylamine and 105 mg (0.55 mmol) of toluenesulfonylchloride was added and stirring was continued for an additional 4 h. The mixture was concentrated and the residue dissolved in ethyl acetate. The organic portion was washed twice each with 1 N NaOH and brine, dried over Na2 SO4 and the product was purified by silica gel chromatography (1:3 v/v ethyl acetate:hexane) to give 274 mg of 20A as a foam.

164148-92-9, As the paragraph descriping shows that 164148-92-9 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc; US5936089; (1999); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.82827-09-6,6-Bromoisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

82827-09-6, To an ice-cooling solution of 6-bromoisoquinolin-1(2H)-one (800 mg, 3.57 mmol) in DMF (8 mL) was added sodium hydride (160 mg, 3.93 mmol, 60%) in small portions, after the addition, the reaction system was warmed up to room temperature and stirred for 20min, iodoethane (800 mg, 5.36 mmol) was added. After the addition, the reaction system was stirred at room temperature for 2h, the reaction was quenched by addition of water (20 mL), extracted with ethyl acetate (20 mL ¡Á 2), the combined organic layers were washed with brine, dried over sodium sulfate, separation of organic phase, dried over anhydrous sodium sulfate, filtered and concentrated, the residue was purified by column chromatography on silica gel (ethyl acetate: petroleum ether = 1:4) to afford compound 15.1 (800 mg, yield: 91%) as a white solid

As the paragraph descriping shows that 82827-09-6 is playing an increasingly important role.

Reference£º
Patent; Shanghai de Novo Pharmatech Co., Ltd.; GAO, Daxin; WANG, Yuxun; CHEN, Shoujun; YANG, Heping; (101 pag.)EP3453707; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.164148-92-9,tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of tert-butyl 6-amino-3,4-dihydroisoquinoline-2(lH)-carboxylate (3 g, 12mmol), 3,5-dibromo-l-methylpyrazin-2(lH)-one (2.68 g, lOmmol), and triethylamine (1.5 g, 15mmol) in IPA (50 mL) was heated at 70C for 15 h. The mixture was cooled to room temperature. The resulting yellow solids were collected by filtration and dried in vacuum to afford 120a as a yellow solid (2.83 g, 65 ).MS: [M+H]+ 435.

164148-92-9, 164148-92-9 tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 2756371, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
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3336-43-4, 1-Chloroisoquinolin-4-ol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Preparation of 1-chloro-4-ethoxyisoquinoline To a solution of 1-chloroisoquinolin-4-ol (1.0 g, 5.5 mmol) in acetonitrile (10 mL) was added K2CO3 (2.3 g, 16.7 mmol) followed by ethyl iodide (0.87 ml, 11.0 mmol) at room temperature. The reaction mixture was stirred at room temperature for overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-ethoxyisoquinoline (0.7 g, 62%) as off-white solid. 1H NMR (400 MHz, CD3OD): delta ppm 8.26-8.24 (m, 2H), 7.79 (s, 1H), 7.76-7.26 (m, 2H), 4.29-4.24 (q, J=6.8 Hz, 2H), 1.58-1.54 (t, J=6.8 Hz, 3H); MS: MS m/z 207.7 (M++1).

3336-43-4, 3336-43-4 1-Chloroisoquinolin-4-ol 4281882, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3482-14-2,Isoquinolin-8-ol,as a common compound, the synthetic route is as follows.

Synthesis of 8-propoxy-isoquinoline (2) To a solution of 8-hydroxy-isoquinoline (1) (1.7 g, 11.7 mmol) in DMF (20 ml) at 0 C was added NaH (940 mg, 23.4 mmol, 2.0 eq.). The mixture was stirred for 30 min. Bromopropane (1.6 ml, 17.6 mmol, 1.5 eq.) was then added. The reaction was allowed to warm to RT and was stirred for 1 h. The reaction was diluted with EtOAc and washed with water. The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash chromatography (cyclohexane/EtOAc 10/0 to 8/2) to afford 1.4 g (63 %) of 8-propoxy-isoquinoline (2) as red oil. 1H NMR (300 MHz,DMSO-d6) delta : 9.66 (s, 1H), 8.52 (d, J = 5.8 Hz, 1H), 8.17 (d, J = 7.1 Hz, 1H), 7.8 (t, J = 8.1 Hz, 1H), 7.65 (d, J = 8.2 Hz, 1H), 7.28 (d, J = 7.8 Hz, 1H), 4.02 (s, 3H)., 3482-14-2

3482-14-2 Isoquinolin-8-ol 135441711, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Sygnis Bioscience GmbH & Co. KG; EP2332917; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6624-49-3,Isoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.

6624-49-3, General procedure: At 0 ¡ãC and with stirring to the solution of 865 mg (5.0 mmol) of isoquinoline-3-carboxylic acid in 10 ml of anhydrous THF 675 mg (5.0 mmol) of HOBt was added to form reaction mixture A. The solution of 5.5 mmol of l-amino acid benzylester in 5 ml of anhydrous THF was adjusted pH 9 with triethylamine and stirred for 30 min to form mixture B. At 0 ¡ãC the mixtures A and B were mixed and then 1339 mg (6.5 mmol) of DCC was added. The reaction mixture was stirred at 0 ¡ãC for 2 h, at room temperature for12 h and TLC (ethyl acetate/petroleum ether, 1:2) indicated the complete disappearance of isoquinoline-3-carboxylic acid. The formed precipitates of DCU were removed by filtration and the filtrate was evaporated under vacumm. The residue was dissolved in 50 ml of ethyl acetate and the formed solution was washed successively with saturated aqueous solution of NaHCO3 (30 ml .x. 3), 5percent aqueous solution of KHSO4 (30 ml .x. 3) and saturated aqueous solution of NaCl (30 ml .x. 3) and dried over anhydrous Na2SO4. After filtration the filtrate was evaporated under vacumm and the residure was purified on silica gel chromatography (CHCl3:MeOH, 20:1) to give the title compounds.

The synthetic route of 6624-49-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zheng, Meiqing; Yang, Yifan; Zhao, Ming; Zhang, Xiaoyi; Wu, Jianhui; Chen, Gong; Peng, Li; Wang, Yuji; Peng, Shiqi; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1672 – 1681;,
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63927-23-1, 5-Bromo-8-nitroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

63927-23-1, 3. Synthesis of 5-bromo-8-nitro-N-methylisoquinolinium iodide; Iodomethane (506 mmol) was added to a solution of 5-bromo-8-nitroisoquinoline (101 mmol) in N,N-dimethylformamide (200 mL) and the reaction mixture was maintained for 16 h at 40 C. The precipitated solids were collected by filtration, washed with ether (2¡Á250 mL), and dried to provide 5-bromo-8-nitro-N-methylisoquinolinium iodide in 83% yield as a red solid.

The synthetic route of 63927-23-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Memory Pharmaceuticals Corporation; US2010/16297; (2010); A1;,
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Isoquinoline | C9H7N – PubChem

23687-26-5, 6-Aminoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

K3P04 (0.481 g, 2.264 mmol), Pd2(dba)3 (0.043 g, 0.0472 mmol) and Xantphos (0.045 g, 0.0786 mmol) were added to a solution of intermediate 6 (0.127 g, 0.786 mmol) in THF (6 mL) while nitrogen was bubbling. After 10 min, isoquinolin-6-amine (0.125 g, 0.865 mmol, CAS 23687-26-5) was added and the mixture was stirred at rt for 10 min. Then, the mixture was heated at 90 ¡ãC for 16 h. After cooling to rt, the mixture was washed with sat. NaHC03 and extracted with EtOAc. The organic layer was dried over MgS04, filtered and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane from 5/95 to 100/0). The desired fractions were collected and concentrated in vacuo. The product was purified by preparative HPLC ((from 59percent H20 (25 mM NH4HC03) – 41 percent MeCN- MeOH to 17percent H20 (25 mM NH4HC03) – 83percent MeCN-MeOH). The desired fractions were collected and concentrated in vacuo. The product was triturated with n-pentane to yield compound 4 as a beige solid (0.075 g, 34percent). NMR (300 MHz, (0207) CHLOROFORM- ) delta ppm 5.69 (d, J=54.6 Hz, 2 H) 6.80 (br s, 1 H) 7.00 (d, J=8.9 Hz, 1 H) 7.39 – 7.47 (m, 1 H) 7.54 (d, J=5.8 Hz, 1 H) 7.89 (d, J=8.8 Hz, 1 H) 7.97 (s, 1 H) 8.22 (d, J=2.1 Hz, 1 H) 8.43 (d, J=5.8 Hz, 1 H) 9.09 (s, 1 H)

23687-26-5, As the paragraph descriping shows that 23687-26-5 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; ANDRES-GIL, Jose, Ignacio; BORMANS, Guy, Maurits, R.; DECLERCQ, Lieven, Denis, Herwig; FIERENS, Katleen; LEENAERTS, Joseph, Elisabeth; MOECHARS, Diederik, Willem, Elisabeth; ROMBOUTS, Frederik, Jan, Rita; KOLB, Hartmuth; ZHANG, Wei; (67 pag.)WO2018/15307; (2018); A1;,
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