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

Participants

Reaction Steps

A solution of 2-(4-chloro-3-nitrobenzoyl)benzoic acid (75 g, 0.25 mol) in ammonium hydroxide 28% (250 mL) was heated to 85° C. for four days. Additions of ammonium hydroxide 28% (80 ml) were made three times daily. The solution was partially concentrated in-vacuo, then cooled in an ice bath. To the solution was added 6N hydrochloric acid until the pH became weakly acidic. The solid which formed was collected by vacuum filtration, washed twice with water (250 mL) and dried to afford 2-(4-amino-3-nitrobenzoyl)benzoic acid (72 g, 100%) as a yellow solid. 1H NMR (400 MHz, d6-DMSO): 8.09 (br s, 3H), 7.99 (d, 1H), 7.75-7.58 (m, 3H), 7.40 (d, 1H), 7.09 (d, 1H); MS (EI) for C14H10N2O4: 309 (MNa+)

Provenance & Evidence