Ethanol → HCID 11822907, compound

Participants

Reaction Steps

A solution of 5-(2,5-dichlorophenyl)-cyclohexane-1,3-dione (5.0 g) and ammonium acetate (4.5 g) in ethanol (100 ml) was refluxed for 20.5 hours. Under reduced pressure, the solvent was evaporated, and the residue was washed with water and toluene and dried to give crystals, which were dissolved in ethanol (50 ml) and toluene (150 ml). To the solution were added 3-oxobutylaldehydedimethylacetal (6.1 g) and powdery 85% potassium hydroxide (1.0 g), and the mixture was refluxed. To the mixture was added powdery 85% potassium hydroxide (0.21 g), 30 minutes later; were added powdery 85% potassium hydroxide (0.21 g) and 3-oxobutylaldehydedimethylacetal(0.24 g), 1 hour later; and powdery 85% potassium hydroxide (0.21 g), 1.5 hours later; and then the mixture was refluxed for 1.5 hours. 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). The resulting crystals were recrystallized from ethyl acetate-hexane to give 7-(2,5-dichlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (3.7 g) as crystals.

Provenance & Evidence