Ethanol → HCID 22897228, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-nitrobenzaldehyde (7-1, 3.00 g, 16.0 mmol, 1 equiv) and 10% palladium on carbon (0.850 g, 0.800 mmol, 0.05 equiv) in ethanol (50 mL) was stirred under a hydrogen balloon for 2 h at 23° C. The catalyst was filtered onto a pad of celite and washed with ethanol (50 mL). The combined filtrate was concentrated to 20 mL, then diethyl malonate (3.92 mL, 25.8 mmol, 1.61 equiv) and piperidine (0.638 mL, 6.45 mmol, 0.403 equiv) were added. The resulting mixture was heated at reflux for 48 h. The mixture was allowed to cool to 23° C., and the precipitate was filtered and washed with cold ethanol (30 mL) to give 6-chloro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester (7-2) as a light yellow solid.

Provenance & Evidence