Ethyl Acetate → 4-Amino-2-fluoro-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-fluoro-N-methyl-4-nitro-benzamide 21 (3 g, 15.1 mmol) in co-solvent of ethyl acetate and acetic acid (12 mL+12 mL) was added iron dust (8 g, 143. mmol). The suspension was heated at reflux until the starting material disappeared in LCMS. Cooled down to 25° C. The solid was filtered off and the filtrate was diluted with ethyl acetate (50 mL). The organic phase was washed with brine (3×30 mL), dried (MgSO4) and concentrated to dryness in vacuo. The title compound 4a was obtained as an orange solid (2.5 g, 97% yield). MS: 169 (M+H)+. 1H NMR (acetone-d6, 500 MHz): δ 7.69 (1H, dd, J=8.7, 8.8 Hz), 7.15 (1H, s), 6.51 (1H, dd, J=8.6, 2.1 Hz), 6.38 (1H, dd, J=14.7, 2.1 Hz), 5.70 (1H, br s), 2.88 (3H, d, J=4.3 Hz).

Provenance & Evidence