2-Chlorobenzaldehyde → 4-(2-Chlorophenyl)-3-ethoxycarbonyl-2-[2-(2-n-propylimidazol-1-yl)propoxymethyl]-1,4,5,6,7,8-hexahydro-5-oxoquinoline

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Reaction Steps

Ethyl 4-[2-(2-n-propylimidazol-1-yl)propoxy]-3-ketobutanoate (590 mg), 3-aminocyclohex-2-enone (220 mg) and 2-chlorobenzaldehyde (281 mg) were stirred in refluxing ethanol (8 ml) for 8 hours. The solvent was removed under reduced pressure. The crude product was chromatographed over silica eluting with a mixture of diethylamine and ethyl acetate (1:49). The solvents were removed in vacuo and the residue rechromatographed over silica eluting with a mixture of methanol and ethyl acetate [1:9]. The solvents were removed in vacuo. The resulting foam was stirred in ether overnight, the solid filtered and dried in vacuo yielding the title compound as a white solid 220 mg (22%). M.p. 127°-131° C.

Provenance & Evidence