Potassium Hydroxide → 7-(2-Chloro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

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Reaction Steps

In ethanol (70 ml) and toluene (120 ml) was dissolved 1-amino-5-(2-chloro-5-methylphenyl)cyclohexen-3-one (2.9 g), and to the solution were added 3-oxobutylaldehydedimethylacetal (4.1 g) and powdery potassium hydroxide (0.5 g). The mixture was refluxed, and to the mixture was added powdery potassium hydroxide (0.14 g), 30 minutes later; were added powdery potassium hydroxide (0.14 g) and 3-oxobutylaldehydedimethylacetal (0.33 g), 1 hour later; and was added powdery potassium hydroxide (0.14 g), 1.5 hours later. The mixture was refluxed at the same temperature 2 hours and cooled. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, ethyl acetate was evaporated, and the residue was purified with silica gel column (ethyl acetate-hexane). The resulting crystals were recrystallized from ethyl acetate-hexane to give 7-(2-chloro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (2.3 g).

Provenance & Evidence