Hydrochloric Acid → 6-Fluoro-3-nitro-2-phenylaminobenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-difluoro-3-nitrobenzoic acid (5 g, 24.6 mmol) in EtOH (25 mL) and water (25 mL) at 0° C. were added Et3N (6.2 mL, 44.3 mmol) and aniline (2.3 g, 24.6 mmol). The reaction mixture was heated at 70° C. for 4 h under a nitrogen atmosphere. After cooling to RT, the pH of the solution was adjusted to 1 by addition of 1N HCl. A precipitate formed and this solid was collected by filtration, washed with water to afford the title compound (6.0 g, 88%). 1H NMR (DMSO-d6, 400 MHz): δ 9.02 (1H, s), 8.18 (1H, dd, J=9.29, 5.78 Hz), 7.25-7.16 (2H, m), 7.05 (1H, t, J=9.07 Hz), 7.00-6.91 (3H, m)

Provenance & Evidence