Ethanol → HCID 18317361, compound

Participants

Reaction Steps

A solution of 5-(3-chloro-2-thienyl)-1,3-cyclohexanedione (0.6 g) and ammonium acetate (0.61 g) in ethanol (20 ml) was refluxed for 13 hours. Under reduced pressure, the solvent was evaporated, and to the residue were added ethyl acetate and water. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethanol (6 ml) and toluene (18 ml). To the solution were added acetylacetoaldehydedimethylacetal (0.86 g) and powdery 85% potassium hydroxide (0.14 g), and the mixture was refluxed. With 30 minutes interval, powdery 85% potassium hydroxide (0.029 g) was added thrice to the mixture, and the mixture was refluxed for 1 hour. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The mixture was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give oil of crude 7-(3-chloro-2-thienyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.3 g).

Provenance & Evidence