Ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)acetate → Ethyl 2-(5-amino-4-fluoro-2-methylphenyl)acetate

Participants

Reaction Steps

Ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)acetate (16.79 g, 69.6 mmol, 1.00) in EtOH (60 ml) was shaken with 10% Pd/C (50% H2O) (7.41 g, 3.48 mmol, 0.050 eq) under H2 (3.5 atm) at RT for 2 h until H2 uptake was complete. The completed reaction was filtered on Celite, rinsing forward with EtOH. The cake was washed well with EtOH and the combined filtrates were concentrated and pumped on to afford ethyl 2-(5-amino-4-fluoro-2-methylphenyl)acetate (13.18 g, 90% yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6): δ 6.80 (d, J=12.4 Hz, 1 H), 6.59 (d, J=9.6 Hz, 1 H), 4.86 (s, 2 H), 4.05 (q, J=7.2 Hz, 2 H), 3.46 (s, 2 H), 2.05 (s, 3 H), 1.17 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 212.2 (M+H)+.

Provenance & Evidence