m-Aminoacetanilide → HCID 69064422, compound

Participants

Reaction Steps

A mixture of 4-fluoro-3-nitrobenzoic acid (5) (10.2 g, 54.9 mmol), N-(3-aminophenyl)acetamide (9.21 g, 66.6 mmol) and Et3N (1.4 mL, 10.1 mmol) in anhydrous EtOH (160 mL) was heated at reflux under N2 overnight. The reaction mixture was then cooled and filtered, and the orange solid collected by filtration. It was then washed with 2 M HCl(aq), and dried in vacuo to give 4-{[3-(acetylamino)phenyl]amino}-3-nitrobenzoic acid. 1H NMR (400 MHz, DMSO-d6): δ 2.03 (s, 3H), 7.02 (d, J=7.9 Hz, 1H), 7.13 (d, J=9.0 Hz, 1H), 7.37 (t, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.68 (s, 1H), 7.93 (dd, J=9.0, 1.9 Hz, 1H), 8.62 (s, 1H), 9.76 (s, 1H), 10.08 (s, 1H), 13.02 (br, 1H); MS (ES+): m/z 316 [MH+]

Provenance & Evidence