Nitric Acid → Methyl 4-acetamido-2-methoxy-5-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To methyl 4-acetamido-2-methoxybenzoate (299 mg, 1.34 mmol) in acetic anhydride (3 ml) stirred under nitrogen at −10° C. was added concentrated nitric acid (0.35 ml) dropwise. After then stirring at 0° C. for 10 min the reaction mixture was partitioned between ethyl acetate (20 ml) and water (20 ml). The aqueous layer was further extracted with ethyl acetate (2×10 ml) and the combined organic extract washed with saturated sodium bicarbonate solution (2×10 ml), brine (2×10 ml), dried (MgSO4) and evaporated to give methyl 4-acetamido-2-methoxy-5-nitrobenzoate (301 mg, 84%) as a dull orange powder.

Provenance & Evidence