2-Amino-3-nitrobenzoic acid → Methyl 2-amino-3-nitrobenzoate

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Reaction Steps

After dissolving 2-amino-3-nitrobenzoic acid (1.00 g, 5.49 mmol) in methanol (40 ml), sulfuric acid (0.50 ml) was added and the mixture was heated to reflux for 2 days. The reaction mixture was cooled to room temperature, and then the pH was adjusted to approximately 9 with saturated aqueous sodium bicarbonate and the mixture was concentrated under reduced pressure to approximately 10 ml. Water (20 ml) was added, the mixture was extracted with ethyl acetate (10 ml×3 times), and the obtained organic layer was dried over anhydrous magnesium sulfate. It was then concentrated under reduced pressure, and the produced crystals were dried to obtain 2-amino-3-nitrobenzoic acid methyl ester. The compound was identified by NMR.

Provenance & Evidence