Acetic Acid → ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

1.31 g of 2-(4-chloro-3-methyl-2-pyridyl)-2-cyclopropylethanal (XII) was dissolved in 45 ml of anhydrous ethanol, and 1.48 ml of piperidine, 1.48 ml of acetic acid and 4.75 ml of diethylmalonate were added thereto and the resulting mixture was heated at 100° C. for 5 hours. The solvent was distilled off under reduced pressure, and thereafter, the resulting mixture was diluted with ether and the resulting organic layer was washed with water and saturated salt water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. 30 ml of Dowtherm A was added to the resulting residue, which was heated at 240° C. for 30 minutes. The reaction solution was purified directly by silica gel column chromatography (eluent; hexane hexane:ethyl acetate=1:1) to obtain 1.45 g of ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (XIII).

Provenance & Evidence