Methyl 2-amino-5-bromobenzoate → 2-Amino-5-bromo-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-amino-5-bromobenzoate (Compound 106B, 65 g) and CH3NH2.H2O (1000 mL) was stirred at 80° C. overnight in a pressure tube. The mixture was diluted with H2O (1000 mL) and extracted with EtOAc (3×500 mL). The combined organic layers were dried over MgSO4, concentrated to afford the title compound (55 g, yield: 87%) as a gray solid. 1H NMR (CDCl3, 400 MHz): δ=2.93 (d, J=5.2 Hz, 3 H), 5.48 (s, br, 2 H), 6.04 (s, br, 1 H), 6.54 (d, J=8.4 Hz, 1 H), 7.24 (dd, J=2.0, 8.4 Hz, 1 H), 7.38 (d, J=2.0 Hz, 1 H).

Provenance & Evidence