Benzyl 2-(3-fluoro-4-nitrobenzamido)acetate → 2-(4-Amino-3-fluorobenzamido)acetic acid

Participants

Reaction Steps

To a solution of benzyl 2-(3-fluoro-4-nitrobenzamido)acetate (200 mg) in EtOAc (10 mL) was added Pd/C (10%, 200 mg) at rt and stirred under the atmosphere of H2 gas for 20 min. Work-up of the reaction mixture as described in example 1 gave product as an off-brown color solid (100 mg, 79%), mp 198-200° C. 1H NMR (400 MHz, DMSO-d6): δ 12.52 (1H, br s), 8.45 (1H, br s), 7.52 (1H, d, J=13.2 Hz), 7.47 (1H, d, J=8.0 Hz), 6.77 (1H, t, J=8.4 Hz), 5.71 (2H, s), 3.87 (2H, d, J=5.2 Hz); 13C NMR (100 MHz, DMSO-d6): δ 171.5, 165.5, 149.5 (d, J=235 Hz), 139.7 (d, J=13.0 Hz), 124.3 (d, J=2.0 Hz), 121.1 (d, J=6.0 Hz), 114.8 (d, J=4.0 Hz), 114.0 (d, J=20.0 Hz), 41.2; LC-MS (negative ion mode): m/z 211 (M−H)−.

Provenance & Evidence