Hydrochloric Acid → Methyl 4-amino-3-methylbenzoate

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Reaction Steps

To a 500 mL round bottomed flask equipped with a stirring bar, reflux condenser and a drying tube was added 3-methyl-4-aminobenzoic acid (8.00 g, 52.92 mmol) and anhydrous methanol (300 mL). This solution was saturated with anhydrous HCl gas and the mixture was stirred at ambient temperature for 26 h. The methanol and HCl were removed in vacuo and the solid product was suspended in 400 mL of EtOAc. This mixture was made basic by careful addition of aqueous NaHCO3 solution. The layers were separated and the organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give methyl 3-methyl-4-aminobenzoate as a yellow solid.

Provenance & Evidence