General steps:
1. dissolve 4-acetamido-2-nitrobenzoic acid (1.80 g, 8.0 mmol) in a mixture of 12 N hydrochloric acid (14 mL) and anhydrous ethanol (10 mL).
2. The reaction mixture was heated to 90-100°C and kept for 5 hours.
3. Upon completion of the reaction, the ethanol is removed by vacuum concentration.
4. The pH of the reaction mixture was adjusted to 4 with 1 N sodium hydroxide solution.
5. The precipitate was collected by filtration to give ethyl 4-amino-2-nitrobenzoate (140 mg, 8% yield).
Product characterization data:
1H-NMR (CDCl3): δ 7.61 (d, J = 8.5 Hz, 1H), 6.82 (d, J = 2.1 Hz, 1H), 6.74 (dd, J = 8.5, 2.1 Hz, 1H), 6.52 (bs, 2H), 4.17 (q, J = 7.1 Hz, 2H), 1.21 (t, J = 7.1 Hz, 3H); MS ( DCI) m/e: 211 (MH+).
