(R)-2-(2-Fluoro-4-nitrobenzamido)propanoic acid → (R)-2-(4-Amino-2-fluorobenzamido)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of iron powder (656 mg, 11.71 mmol) in AcOH (6 mL) was added (R)-2-(2-fluoro-4-nitrobenzamido)propanoic acid (300 mg, 1.17 mmol) at rt and stirred at 60-70° C. for 20 min. Work-up of the reaction mixture as described in example 6 gave the product as a white color solid (190 mg, 72%). 1H NMR (400 MHz, DMSO-d6): δ 7.68 (1H, br s, exchangeable with D2O), 7.56 (1H, t, J=9.0 Hz), 6.41 (1H, d, J=8.8 Hz), 6.31 (1H, d, J=15.2 Hz), 5.99 (2H, br s, exchangeable with D2O), 4.15 (1H, br s), 1.30 (3H, d, J=6.8 Hz); LC-MS (negative ion mode): m/z 225 (M−H)−.

Provenance & Evidence