Methyl 5-fluoro-3-methyl-2-nitrobenzoate → Methyl 2-amino-5-fluoro-3-methylbenzoate

Participants

Reaction Steps

A solution of methyl 5-fluoro-3-methyl-2-nitrobenzoate (8.4 g, 39.4 mmol) from Step B above in methanol (150 mL) was purged with nitrogen. Palladium on charcoal was added to the solution and hydrogenation was carried out for 24 h at 1 atm. The reaction mixture was filtered through a pad of Celite and washed with methanol. The filtrate was concentrated in vacuo to afford methyl 2-amino-5-fluoro-3-methylbenzoate (6.8 g, 94%) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.32 (dd, J=10.0, 3.0 Hz, 1H), 7.17 (dd, J=9.0, 3.0 Hz, 1H), 6.40 (s, 2H), 3.80 (s, 3H), 2.13 (s, 3H); MS (ESI+) m/z 184 (M+H).

Provenance & Evidence