Pyridine → N-(5-Methoxy-2-methylphenyl)alpha-methylcinnamamide

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Reaction Steps

2-Amino-4-methoxytoluene (13.2 g, 89.7 mmol) and pyridine (10 ml) were dissolved in acetone (112 ml), to which α-methylcinnamoylchloride (19.4 g, 107.6 mmol) was added while cooling and stirring. The mixture was stirred overnight at room temperature. The solvent was evaporated, and the residue was dissolved in chloroform, washed with water, dried, and condensed. The residue was purified by alumina chromatography (chloroform), and subjected to recrystallization with chloroform--n-hexane to obtain 21.27 g of the title compound as colorless crystals (84.4%).

Provenance & Evidence