Ethanol → 5-Amino-2-methylbenzoic acid

Participants

Reaction Steps

To a 250 mL round-bottomed flask was added 2-methyl-5-nitrobenzoic acid (5.0 g, 28 mmol) and palladium 10% on carbon (1.5 g, 14 mmol). The mixture was taken up in EtOAc (30 mL) then EtOH (70 mL) was added. The mixture was purged with H2 then allowed to stir at 1 atm. H2 for 24 h. LCMS indicated about 10% conversion to product. About 0.5 g 10% Pd/C and ˜30 mL MeOH was added to the reaction. The reaction was purged with H2 and let to stir at 1 atm H2 for 20 h. They reaction was monitored for complete conversion by LCMS. The mixture was passed through a pad of celite, washing with MeOH and concentrated to afford 5-amino-2-methylbenzoic acid as an off-white solid MS m/z found 152.1 (ESI, neg. ion).

Provenance & Evidence