Acetic Acid → N-[2-(2-pyridyl)ethyl]-2-methyl-4-hydroxyaniline

Participants

Reaction Steps

A mixture of 50.0 g (0.4 mole) of 2-methyl-4-hydroxyaniline, 2.4 g of glacial acetic acid and 125.0 ml of anhydrous methyl alcohol was heated to reflux with stirring and 63.1 g (0.6 mole) of 2-vinylpyridine was added dropwise to the mixture. The resultant reaction mixture was maintained at reflux for approximately forty-eight hours, cooled to ambient temperature and added to a mixture of aqueous sodium bicarbonate and toluene. The water layer was separated from to toluene layer and the water layer was extracted a second time with toluene. The two toluene layers were combined, washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solid, which crystallized from the toluene upon standing, was collected by filtration, washed with hexane and dried to obtain 23.6 g of N-[2-(2-pyridyl)ethyl]-2-methyl-4-hydroxyaniline (Formula VI: R1 =R9 =H; R2 =CH3 ; R11 =OH), a pale beige-colored solid which melted at 137.5° to 139.5° C. after recrystallization from toluene. Significant infrared maxima appeared at 3200 cm-1 (OH;m) and 1601 cm-1 (C=C;m). The nuclear magnetic resonance spectrum was in accord with the assigned structure.

Provenance & Evidence