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

Participants

Reaction Steps

To a solution of benzyl 2-(2-fluoro-4-nitrobenzamido)acetate (100 mg) in EtOAc (10 mL) was added Pd/C (10%, 100 mg) at rt and stirred under the atmosphere of H2 gas for 30 min. The reaction mixture was filtered and washed with EtOAc (2×5 mL). The residue obtained after evaporation of the solvents was recrystallized from EtOAc to give the product as a white color solid (50 mg, 79%), mp 194-196° C. 1H NMR (400 MHz, DMSO-d6): δ 12.53 (1H, br s), 7.74-7.78 1H, m), 7.52 (1H, t, J=8.8 Hz), 6.42 (1H, dd, J=8.4, 1.6 Hz), 6.31 (1H, d, J=14.4 Hz), 5.99 (2H, s), 3.90 (2H, d, J=5.6 Hz); 13C NMR (100 MHz, DMSO-d6): δ 171.3, 163.4 (d, J=3.0 Hz), 161.7 (d, J=244 Hz), 153.8 (d, J=13.0 Hz), 131.9 (d, J=5.0 Hz), 109.6, 107.8 (d, J=12.0 Hz), 99.1 (d, J=26.0 Hz), 41.3; LC-MS (negative ion mode): m/z 211 (M−H)−.

Provenance & Evidence