2-Oxocyclohexanecarbaldehyde → Dimethyl 5,6,7,8-tetrahydroquinoline-2,3-dicarboxylate

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Reaction Conditions

Reaction Steps

A mixture of 10.04 g dimethyl aminofumarate and 8.0 g 2-formylcyclohexanone is heated at 150° C. under a reflux condenser for one hour. The condenser is removed, and the volatile components allowed to escape. Material volatile at 0.5 mm and 150° C. is then removed. The residue is purified by flash chromatography on silica gel using hexane-ethyl acetate (4:1) as eluant. Fractions containing the product are combined to give 2.97 g dimethyl 5,6,7,8-tetrahydroquinoline-2,3-dicarboxylate as an amber oil having the appropriate NMR and IR spectra.

Provenance & Evidence