Methyl 4-amino-2-fluoro-5-nitrobenzoate → Methyl 4,5-diamino-2-fluorobenzoate

Participants

Reaction Steps

A suspension of methyl 4-amino-2-fluoro-5-nitrobenzoate (6.84 g, 31.9 mmol) and 10% Pd/C (1.2 g) in methanol (200 mL) was hydrogenated under an atmosphere of hydrogen (balloon) for 20 h, filtered through Celite and the filtrate concentrated in vacuo to a residue. The residue was purified by flash chromatography (20% EtOAc/DCM) to afford the desired methyl 4,5-diamino-2-fluorobenzoate as a pink solid (2.36 g, 40%). 1H NMR (CDCl3) δ 7.90 (s, 1H), 7.93 (s, 1H), 7.13 (d, J=8.7 Hz, 1H), 6.88 (s, 1H), 6.37 (d, J=13.5 Hz, 1H), 3.60 (t, J=6.9 Hz, 2H), 2.86 (t, J=6.9 Hz, 12H).

Provenance & Evidence