Water → HCID 59455904, compound

Participants

Reaction Steps

To a solution of N-(4-bromo-2,6-dimethyl-phenyl)-4-fluoro-3-nitro-benzamide (18.3 g, 49.8 mmol) (Example I1) in N,N-dimethylformamide (115 ml) was added sodium cyanide (2.7 g, 54.8 mmol). The reaction mixture was stirred at ambient temperature for 4 hours, then heated to 60° C. for 16 hours. More sodium cyanide (0.73 g, 14.8 mmol) was added and the reaction mixture was heated to 60° C. for a further 8 hours. The reaction mixture was cooled to ambient temperature before the addition of water (200 ml) and ethyl acetate (100 ml). The organic extract was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1), yielding N-(4-bromo-2,6-dimethyl-phenyl)-4-cyano-3-nitro-benzamide (11.8 g, 63% yield). LC/MS (Method A): 374 (MH+). 1H-NMR (400 MHz, DMSO-d6): 8.91 (s, 1H), 8.53 (d, 1H), 8.4 (d, 1H), 7.4 (s, 2H), 2.2 (s, 6H) ppm.

Provenance & Evidence