Dimethylamine → 4-(dimethylamino)-3-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluoro-3-nitrobenzoic acid (1 g; 5.4 mmol) in EtOH (5 mL) was added dimethylamine (730 mg; 16.2 mmol). The resulting mixture was stirred at RT for 18 h and 4 h at 70° C. The reaction mixture was then partitioned between water (10 mL) and Et2O (15 mL), washed with Et2O (10 mL). The aqueous phase was acidified to pH ˜5 with AcOH and washed with Et2O (2×15 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to give the title compound as a yellow powder (1.02 g, 90%). 1H NMR (DMSO-d6, 300 MHz) δ 12.9 (bs, 1H), 8.24 (d, J=2 Hz, 1H), 7.92 (dd, J=8.9, 2 Hz, 1H), 7.20 (d, J=8.9 Hz, 1H), 2.92 (s, 6H). HPLC (Method A) Rt 2.44 min (purity: 97.2%).

Provenance & Evidence