1,2-Benzenedicarboxylic acid, 4-nitro-, 1,2-dimethyl ester → Dimethyl 4-aminophthalate

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Reaction Steps

Palladium on activated charcoal (10% Pd, 200 mg) was added to a solution of 4-nitrophthalic acid dimethyl ester (2.0 g, 8.37 mmol) in methylene chloride (100 ml). The mixture was hydrogenated in a Parr apparatus at 207 kPa (30 psi) for 1½ hour. The mixture was filtered and evaporated to dryness in vacuo to give 4-aminophthalic acid dimethyl ester as white crystals (yield: 1.75 g (100%)). Mp: 83-85° C. 1H—NMR (CDCl3) in ppm: δ 3.80 (3H,s); 3.87 (3H,s); 6.6-6.7 (2H,m); 7.68 (1H,d).

Provenance & Evidence