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

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Reaction Steps

20% Pd(OH)2 (0.50 g) was carefully wetted down under argon with methanol (5 mL) and then 3-(methoxycarbonyl)-5-nitrobenzoic acid (5.00 g, 22.2 mmol) in methanol (20 mL) was added. The mixture was then hydrogenated on a Parr Shaker apparatus for 5 hours at 50 psi. Under argon, the reaction was carefully filtered through a fiberglass filter paper. The filtrate was concentrated to give 3-amino-5-(methoxycarbonyl)benzoic acid (4.0 g, 20.5 mmol, 92% yield) of off-white solids as product. MS found: (M−H)+=194.

Provenance & Evidence