Hydrochloric Acid → 6-Hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

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Reaction Steps

A mixture of 6-methoxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.957 g) and aluminum chloride (3.359 g) in benzene (42 ml) was heated at 60° to 65° with stirring for 4 hours. To the aluminum chloride complex was added a mixture of crushed ice and 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (30 g) with a mixture of chloroform and methanol (50:1 to 10:1) as an eluent. The eluates were evaporated in vacuo to give 6-hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.52 g).

Provenance & Evidence