5-Fluoro-2-nitrobenzoic acid → 2-Amino-5-fluorobenzoic acid

Participants

Reaction Steps

To a pressure flask capable of withstanding, 150 psi. was added 5-fluor-2-nitrobenzoic acid (2.0 g, 0.01 1 mol) dissolved in ethanol (40 mL) and 10% palladium on carbon (200 mg). The reaction was placed in a Parr apparatus and the flask flushed three times with hydrogen leaving an internal pressure of 65 psi. The reaction was continued for 16 hours while maintaining a pressure of 65 psi. The reaction was filtered through celite, washed with ethanol and the filtrate evaporated to dryness to give 2-amino-5-fluorobenzoic acid (1.22 g, 73%) as an off-white solid.: m.p. 183°-184°; 1H NMR (400 MHz, DMSO-d6) δ 6.75 (dd, 1H), 7.16 (dt, 1H), 7.36 (dd, 1H); 13C NMR (100 MHz, DMSO-d6) δ 109.3, 109.4, 115.4, 115.6, 117.8, 117.9, 121.5, 121.9, 148.3, 150.8, 153.8, 168.6, 168.7.

Provenance & Evidence