1,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl ester → 3-Amino-5-(methoxycarbonyl)benzoic acid

Participants

Reaction Steps

A suspension of 3-(methoxycarbonyl)-5-nitrobenzoic acid (11.25 g, 50 mmol) and palladium on carbon (10 wt %, 1.0 g) in MeOH (10 mL) was shaken in hydrogenator under hydrogen at 50 psi for 3 h. The mixture was filtered and concentrated in vacuo to give the title compound (8.0 g, 82% yield): 1H NMR (CD3OD, 500 MHz) δ ppm 3.91 (3H, s), 7.53 (1H, m), 7.55 (1H, m), 7.92 (1H, m). HPLC retention time: 0.922 min (method A). MS (ESI) (M+H)+ 196.12.

Provenance & Evidence