Nitric Acid → Methyl 3-acetylamino-6-bromo-2-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-acetylamino-2-bromo-benzoic acid methyl ester (ii, 5.44 g, 20.0 mmol) in H2SO4 (50 mL) at 0° C. was added HNO3 (50 mL). The reaction mixture was stirred at 0° C. for 20 min and poured into ice water (200 mL). The mixture was then extracted with EtOAc (3×200 mL). The combined extracts were washed with saturated aqueous NaHCO3 (3×200 mL), H2O (3×200 mL), brine (1×200 mL), and dried with Na2SO4. Flash column chromatography gave the desired product iii as a yellow solid (3.60 g, 57%). 1H NMR (acetone-d6): δ 9.47 (br s, 1H), 8.02 (d, J=9.0 Hz, 1H), 7.89 (d, J=9.0, 1H), 3.84 (s, 3H), 2.10 (s, 3H). Anal. Calcd for C10H9BrN2O5: C, 37.88; H, 2.86; N, 8.83. Found: C, 38.02; H, 2.74; N, 8.74.

Provenance & Evidence