Trifluoroacetic acid → Methyl 2-amino-6-chloro-3-nitrobenzoate

Participants

Reaction Steps

A solution of methyl 6-chloro-2-[(4-methoxybenzyl)amino]-3-nitrobenzoate (13.2 g, 37.6 mmol) and TFA (75 mL) was stirred at room temperature for 1.7 h. The mixture was diluted with EtOAc (500 mL) and water (250 mL). Solid NaHCO3 (125 g) was slowly added to the heterogeneous mixture. Saturated aqueous NaHCO3 solution (200 mL) and EtOAc were added and the phases were separated. The organic layer was washed with saturated aqueous NaHCO3 solution (150 mL) and brine (50 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (10-40μ silica gel; hexane:EtOAc 5:1) to yield the title compound (7.03 g, 81% yield) as a yellow solid.

Provenance & Evidence