Methyl 4-amino-3-methoxybenzoate

5081-37-8

41608-64-4

The general procedure for the synthesis of methyl 4-amino-3-methoxybenzoate from methyl 3-methoxy-4-nitrobenzoate was as follows: methyl 3-methoxybenzoate (83.0 g, 500 mmol) was added drop-wise to a mixture of acids consisting of HNO3 (65% by weight, 40 ml) and H2SO4 (70% by weight, 200 ml) at 0 °C. The reaction mixture was stirred overnight and poured into ice water. The mixture was filtered and the solid filter cake was washed with water (3 x 300 ml) to give 84.4 g of methyl 4-nitro-3-methoxybenzoate as a yellow solid in 80% yield. Next, an ethanol (1500 ml) solution of methyl 4-nitro-3-methoxybenzoate (84.4 g, 400 mmol) was stirred with Pd/C (10% Pd, 5.35 g) catalyst for 5 h under H2 atmosphere. After completion of the reaction, the catalyst was removed by Celite filtration. The solvent was evaporated in vacuum to give an off-white solid. Finally, the off-white solid was recrystallized from methanol to give methyl 4-amino-3-methoxybenzoate (70.95 g, 392 mmol) in 98% yield.