Acetic Acid → 2-Amino-3-iodo-4-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

3-Iodo-4-methyl-2-nitrobenzoic acid (46.00 g, 150 mmol) was suspended in ethanol (500 mL) and acetic acid (86 mL, 1498 mmol). The mixture was heated to 70° C. and iron (33 g, 599 mmol) was added in small portions. Stirring was continued for 3 h, and then the reaction was cooled down to RT and poured on 1.5 kg of crushed ice and 1 L of 5 N aqueous HCl. The mixture was extracted with ethyl acetate and the organic layer was dried with sodium sulfate, concentrated under vacuum and dried to give 2-amino-3-iodo-4-methylbenzoic acid (40 g, 96%) as a tan solid. MS (M+H)+ 278

Provenance & Evidence