HCID 66889382, compound → HCID 66889371, compound

Participants

Reaction Steps

A solution of methyl 3-(acetyloxy)-4-(methyloxy)-5-nitrobenzoate (27.2 g, 101 mmol.) in ethyl acetate (200 mL) with 10% palladium on carbon (1.0 g) added was hydrogenated at atmospheric pressure until complete reduction to the aniline was observed by TLC (>24 hours). The mixture was then filtered through a bed of celite and the filtrate concentrated to provide methyl 3-(acetyloxy)-5-amino-4-(methyloxy)benzoate (19.8 g, 82% yield) as an oil that slowly crystallized on standing. 1H NMR (400 MHz, CDCl3): 7.30 (d, 1H), 7.14 (d, 1H), 3.97 (br d, 2H), 3.85 (s, 3H), 3.82 (s, 3H), 2.34 (s, 3H).

Provenance & Evidence