Methanol → Methyl 5-amino-2-hydroxybenzoate

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Reaction Steps

5-Amino-2-hydroxybenzoic acid (10 g, 65.3 mmol) was suspended in MeOH (150 ml), and aqueous 96% sulfuric acid (12 ml, 225 mmol) was added drop wise. The mixture was heated to reflux for 96 hours. After cooling to RT, the solvent was partially removed under vacuum; the remaining solution was basified with NaHCO3 5% and extracted with EtOAc. The organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated under vacuum affording methyl 5-amino-2-hydroxybenzoate as a solid (9.68 g, 57.9 mmol, 89% yield, MS/EST+168.0 [MH]+).

Provenance & Evidence