[OH-].[Na+].C([NH:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([F:19])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])(=O)C.Cl>O>[NH2:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([F:19])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]A solution containing sodium hydroxide (1.5 g, 38.0 mmol) and water (20 mL) was added to 2-acetamido-5-fluoro-3-nitrobenzoic acid (2.055 g, 8.50 mmol) and allowed to reflux for 4 hours. The reaction was cooled to 0° C. and the solution was acidified with concentrated hydrochloric acid. The precipitate which developed was collected by filtration and dried to give 2-amino-5-fluoro-3-nitrobenzoic acid (1.49 g, 88%) as a light yellow solid which is identical in all respects to the compound in Method A.: m.p. 218°-220°; 1H NMR (400 MHz, DMSO-d6) δ 8.04 (dd, 1H), 8.17 (dd, 1H), 8.35 (bs, 1H); 13C NMR (100 MHz, DMSO-d6) δ 118.1, 118.4, 127.5, 127.7, 132.2, 132.3, 144.6, 149.0, 151.4, 168.1; 1R (neat) 3459, 3345, 1687, 1563, 1513, 1440, 1270, 1211 cm-1.
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