Hydrochloric Acid → 2,4-Dimethylquinolin-8-ol

Participants

Reaction Steps

In a three-necked flask were placed 33 g of o-aminophenol and 207 g of concentrated hydrochloric acid and the mixture was heated to the reflux temperature and stirred for 1 hour. To the mixture being heated under reflux was slowly added 51 g of 3-penten-2-one with a purity of 65% over 2 hours and stirring was continued for another 2 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature, 300 ml of a 48% aqueous solution of NaOH was added until the aqueous phase became alkaline. Ethyl acetate was added further, the organic layer was recovered and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by gas chromatography, recrystallized from hexane and the crystals collected by filtration were washed with hexane and dried at 80° C. under reduced pressure to give 18.9 g of 2,4-dimethyl-8-quinolinol.

Provenance & Evidence