Water → 4-[(Pyridin-4-yl)methyl]isoquinolin-1(2H)-one

Participants

Reaction Steps

In the presence of 5×40 g of Raney nickel (added at intervals), 163 g (617 mmol) of 2-[(1-cyano-2-(pyridin-4-yl)-vinyl]-benzoic acid methyl ester are hydrogenated in 3 liters of THF at 40° C. for 90 hours. The reaction mixture is filtered, and the filtrate is concentrated by evaporation and crystallised from acetonitrile/ethyl acetate (→title compound). Further product can be obtained from the mother liquor by chromatography (SiO2; ethyl acetate→acetone): m.p. 189-190° C.; FAB-MS: (M+H)+=237; 1H NMR (DMSO-d6) 11.27 (sb, HN), 8.45 (d, 2H), 8.23 (d, 1H), 7.65 (t, 1H), 7.48 (m, 2H), 7.27 (d, 2H), 7.18 (s, 1H), 4.05 (s, 2H); Anal. calc. (Cl5H12N2O.0.05 H2O) C 75.96%, H 5.14%, N 11.81%; found C 75.8%, H 5.2%, N 11.9%.

Provenance & Evidence