Methanol → Methyl 4-amino-3-hydroxybenzoate hydrochloride

Participants

Reaction Steps

To an anhydrous methanol (100 ml) was added thionyl chloride (14.0 ml) at −10° C. during 20 minutes. After stirring the mixture for 15 minutes, 3-hydroxy-4-aminobenzoic acid (10.0 g) was added at the same temperature. The appeared suspension was stirred at room temperature overnight. The mixture was concentrated and then azeotroped with methanol (50 ml, twice). To the residue was added diethyl ether, and the residue was collected by suction filtration in washing with diethyl ether to give the title compound (12.8 g) having the following physical data.

Provenance & Evidence