Sulfuric Acid → 2-Amino-4,6-dimethoxybenzamide

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (6.52 g, 4.4 mL) was charged to a flask equipped with a magnetic stirring bar and thermocouple. Sulfuric acid (96%, 9.2 g, 5 mL) was charged to the flask. In small portions 2-amino-4,6-dimethoxybenzonitrile (1.01 g, ˜76% pure) was charged to the mixed acid solution in the flask. A condenser was added and the solution was heated at 75° C. for 17 h. After the dark mixture had cooled to room temperature it was charged to water (9.79 g) cooled in a large ice bath while maintaining the reaction temperature below 10° C. Concentrated ammonium hydroxide (19.37 g) was added dropwise to the cooled solution (reaction temperature kept below 15° C.). The solution was then extracted two times with dichloromethane. The organic extracts were dried over MgSO4 and evaporated to yield the desired product (0.45 g) as a light brown solid.

Provenance & Evidence