Ethyl 3-(benzylamino)-4-nitrobenzoate → Ethyl 4-amino-3-(benzylamino)benzoate

Participants

Reaction Steps

To a stirring solution of ethyl 3-(benzylamino)-4-nitrobenzoate (1.52 g, 5 mmol) in ethanol (50 mL) and acetic acid (7 mL) was added zinc dust (2.3 g, 35 mmol). After 1 hr at room temperature, the solids were filtered and the remaining solution was concentrated. The resulting residue was diluted with ethyl acetate (200 mL) and washed with dilute aq. NaHCO3 (1×100 mL), then the organic layer was dried (MgSO4), filtered and then concentrated to provide 1.44 g (˜100%) of crude ethyl 4-amino-3-(benzylamino)benzoate as an orange/brown oil. This material was used without further purification.

Provenance & Evidence