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