HCID 136340693, compound → HCID 178509732, compound

Participants

Reaction Steps

5% Palladium on carbon (0.5 g) was added to a solution of (E)-4-(2-(5-nitro-1H-imidazol-4-yl)vinyl)benzonitrile (10 g, 0.04 mol) in methanol (500 mL) and the resulting mixture hydrogenated at atmospheric pressure for 24 hours. The catalyst was removed by filtering through a short bed of Celite™, and the Celite™ washed with 10% MeOH/DCM (200 mL). The filtrate was evaporated to dryness and purified by column chromatography (10% MeOH/DCM) to leave the product as a yellow/brown solid (6 g, 69%). δH (DMSO-d6) 11.76 (1H, bs, NH), 7.70 (2H, d, J=8.4), 7.50 (2H, d, J=8.4), 7.44 (1H, d, J=16.0), 7.36 (1H, s), 6.42 (1H, d, J=16.0), 5.17 (2H, bs, NH2); IR (cm−1) 2220 (CEN), 1629 (C═C); MS (m/z) 211.0969 (C12H11N4 (M+1)) requires 211.0984.

Provenance & Evidence