Hydrochloric Acid → 2-(4-Amino-3-nitrobenzoyl)benzoic acid

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Reaction Steps

A solution of 2-(4-chloro-3-nitrobenzoyl)benzoic acid (38.5 g, 0.126 mol) in ammonium hydroxide (33% wt, 200 mL) was heated to a gentle reflux and stirred for 24 h. An additional ammonium hydroxide (200 mL) was added every 5 h within the 24 h reaction time period. The reaction mixture was cooled to room temperature and was added 6N aqueous hydrochloric acid until pH reached 2. The precipitated yellow solid was collected by filtration and washed with water then dried in vacuo to provide 2-[(4-amino-3-nitrophenyl)carbonyl]benzoic acid (38.8 g, 95%). 1H NMR (400 MHz, CD3OD): 8.27 (d, 1H), 8.11 (d, 1H), 7.80 (dd, 1H), 7.72 (td, 1H), 7.65 (td, 1H), 7.39 (d, 1H), 7.01 (d, 1H); MS (EI) for C14H10N2O5: 309 (MNa+).

Provenance & Evidence