Ammonium Chloride → Methyl 3-Amino-5-bromo-2-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To stirred solution of methyl 5-bromo-2-methyl-3-nitrobenzoate (290 g, 1060 mmol) in ethanol (1.5 L) was added aqueous ammonium chloride (283 g, 5290 mmol dissolved in 1.5 L water). The resulting mixture was stirred and heated at 80° C. followed by addition of iron powder (472 g, 8450 mmol) in portions at 80° C. The resulting reaction mixture was heated at 80° C. for 12 h. After completion, the reaction mixture was hot filtered over celite and the celite bed was washed with methanol (5 L) followed by washing with 30% MeOH in DCM (5 L). The combined filtrate was concentrated in-vacuo, the residue obtained was diluted with aqueous bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to afford the title compound as brown solid (220 g, 89% yield).

Provenance & Evidence