Hydrochloric Acid → Methyl 2-amino-3-nitrobenzoate

Participants

Reaction Steps

Sodium methoxide (1.50 g, 27.7 mmol) was added to a solution of methyl-2-(acetylamino)-3-nitrobenzoate (1.0 g, 4.2 mmol) in MeOH (30 ml) and the mixture stirred at ambient temperature under nitrogen for 16 h. The reaction was cautiously acidified with concentrated hydrochloric acid then heated at reflux overnight, followed by evaporation and re-evaporation by toluene (2×30 ml). The residue was treated with CH2Cl2 (50 ml), the insoluble material removed through filtration and the filtrate reduced in vacuo. The residue was purified by flash column chromatography [SiO2, EtOAc-hexane (1:4, 1:0)] affording methyl-2-amino-3-nitrobenzoate (535 mg) as a bright yellow solid.

Provenance & Evidence