Ethyl 3-chloro-3-oxopropionate → 6-Chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 9 (0.13 g, 0.38 mmol) in 3 mL of anhydrous benzene was treated with ethyl-3-chloro-3-oxopropionate (54 μL, 63.0 mg, 0.421 mmol). The reaction mixture was heated to 80° C. for 1 h. The reaction was allowed to cool to room temperature and was concentrated in vacuo. The resulting oil was dissolved in 3 mL of ethanol, treated with NaOEt (40.0 mg, 0.59 mmol). The suspension was heated to 80° C. for 10 min, allowed to cool to room temperature, and diluted with H2O. The resulting precipitate was filtered to give 10 (63.0 g, 43%) as a white solid.

Provenance & Evidence