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 4-vinylpyridine was added dropwise. The resulting reaction mixture was refluxed approximately seventy-two hours. After cooling the reaction mixture to ambient temperature, the solid was collected by filtration, washed twice with fresh methanol, and dried in vacuo to obtain 30.9 g of N-2-[2-(4-pyridyl)ethyl]-2-methyl-4-hydroxyaniline (Formula VI: R1 =R9 =H; R2 =CH3 ; R11 =OH), a colored solid which melted at 146°-148.5° C. A significant infrared maximum appeared at 3410 cm-1 (OH;m). The nuclear magnetic resonance spectrum was in accord with the assigned structure.

Provenance & Evidence