4-Amino-2-nitro-benzoic acid ethyl ester

Synthesis

64-17-5

21573-29-5

84228-46-6

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+).

References