Allyl bromide → HCID 21555662, compound

Participants

Reaction Steps

A well-stirred mixture of 65.1 parts of ethyl-4-hydroxy-quinoline-2-carboxylate, 42 parts of anhydrous potassium carbonate, 38.4 parts of allyl bromide and 800 parts of acetone was boiled under reflux for 24 hours. The cooled reaction mixture was filtered to remove inorganic salts and acetone was removed by evaporation under reduced pressure. A solution of the residual brown oil in ether (360 parts) was washed successively with N-sodium hydroxide solution (3 portions each comprising 50 parts) and water (4 portions each of 100 parts), then dried over magnesium sulphate and evaporated to remove solvent. The resultant viscous oil crystallised on cooling and the crystals were recrystallised from light petroleum (60°-80°C) to yield 57.1 parts of ethyl 4-allyloxyquinoline-2-carboxylate as pale yellow needles, m.pt. 71°-72°C.

Provenance & Evidence