Ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetate → Ethyl 2-(5-amino-2-chloro-4-fluorophenyl)acetate

Participants

Reaction Steps

A solution of ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetate (22.5 g, 86.2 mmol) in ethanol (200 mL) was stirred with Raney Ni (20% slurry in water, ˜5.0 g, 17 mmol) under a hydrogen atmosphere (30 psi) for 5 h. The catalyst was removed by filtration and the filtrate was concentrated to give ethyl 2-(5-amino-2-chloro-4-fluorophenyl)acetate (19 g, 95% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.10 (d, J=11.2 Hz, 1 H), 6.71 (d, J=9.2 Hz, 1 H), 5.27 (s, 2H), 4.05 (q, J=6.8 Hz, 2 H), 3.57 (s, 2 H), 1.14 (t, J=6.8 Hz, 3 H); MS (ESI) m/z: 232.0 [M+H]+.

Provenance & Evidence