Methanol → Methyl 3-amino-4-methoxybenzoate hydrochloride

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Thionyl chloride (8.7 mL) is added dropwise to methanol (90 mL) at −30° C. under argon gas atmosphere over a period of 15 minutes and a mixture is stirred at −20° C. for 30 minutes. To the mixture is added 3-amino-4-methoxybenzoic acid (5.0 g) and the solution is stirred at the same temperature for 15 minutes and at room temperature for 3 days. The reaction mixture is concentrated in vacuo and the resultant crystals are washed with methanol/ether to give methyl 3-amino-4-methoxybenzoate hydrochloride (6.25 g, yield; 96%) as colorless crystals. M.p. 213-215° C., MS (APCI) m/z: 182 [M+H]+

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