Hydrochloric Acid → Methyl 3-methylanthranilate

Participants

Reaction Conditions

Reaction Steps

A solution of 60.8 g of 2-amino-3-methylbenzoic acid in 900 ml of dry methanol was saturated with anhydrous hydrogen chloride at 0°-10° C., then allowed to stand at room temperature overnight. Then it was refluxed for one hour, cooled to 5° C., resaturated with anhydrous hydrogen chloride, held overnight at room temperature and stripped of solvent. The residue was made neutral with saturated aqueous sodium bicarbonate solution, and extracted with methylene chloride. The extract phase was washed with saturated aqueous sodium bicarbonate solution, dried (MgSO4), filtered and stripped of solvent. The residue was distilled in a kugelrohr apparatus to give methyl 2-amino-3-methylbenzoate (49A), b.p.: 100°-105° C. (1Torr.).

Provenance & Evidence