Methyl iodide → 4-(Methyl(phenyl)amino)benzoic acid

Participants

Reaction Steps

NaH 60% dispersed in mineral oil (0.030 g; 0.745 mmol) was added to a solution of methyl 4-(phenylamino)benzoate (0.113 g; 0.497 mmol) in THF (3 mL). After stirring the resulting solution for 10 minutes, methyl iodide (0.062 mL; 0.994 mmol) was added and the resulting mixture was stirred overnight at room temperature. The mixture was diluted in water and extracted with ethyl acetate. The organic layer was washed with brine and dried to yield 0.045 g (40%) of the title compound as a white solid.

Provenance & Evidence