3-Aminocyclohex-2-en-1-one → 3-Methyl-7,8-dihydroquinolin-5(6H)-one

Participants

Reaction Steps

A mixture of 3-aminocyclohex-2-enone (11.1 g., 0.1m) and 3-ethoxy-2-methylacrolein (11.4 g, 0.1m) was heated at 120° for 16 hours in a flask equipped for downward distillation. The ethanol-water distillate (6.5 ml.) was discarded and the residual oil distilled at 0.2 mm Hg to give 3-methyl-7,8-dihydro-5(6H)quinolone as a colourless oil b.p. 78°-80° (7.8 g, 48%) which solidified on standing and was recrystallized from 40- 60° petroleum ether as colourless needles m.p. 45°. Found: C, 74.81; H, 6.97; N, 8.91%. C10H11NO requires: C, 74.51; H, 6.88; N, 8.69%.

Provenance & Evidence