Triethylamine → 3-Methyl-7,8-dihydroquinolin-5(6H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of cyclohexane-1,3-dione (22.4 g., 0.2 mol.), 3-amino-2-methylacrolein (17 g., 0.2 mol.), triethylamine (10 ml.) and piperidinium acetate (0.25 g.) was heated with stirring in an oil bath at 120° C for 24 hours. The cooled reaction mixture was dissolved in 2N HCl (50 ml.) and extracted with ethyl acetate (3 × 50 ml.) and the organic extracts discarded. The aqueous solution was adjusted to pH 10 with sodium carbonate and extracted with chloroform (3 × 50 ml.). The combined extracts were dried (MgSO4) and the solvent removed in vacuo. The residual oil was distilled to give the title compound as a colourless oil (17 g., 52%) b.p. 79°/0.2 mm Hg which solidified.

Provenance & Evidence