m-Aminoacetanilide → HCID 69064422, compound

Participants

Reaction Steps

A mixture of 4-fluoro-3-nitrobenzoic acid (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 atmosphere. After 16 h, the reaction mixture was cooled and the resultant precipitate filtered. The orange solid was washed with 2 M aq HCl and dried to yield 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 (brs, 1H). MS (ES+): m/z 316 [MH+].

Provenance & Evidence