Hydrochloric Acid → HCID 70524412, compound

Participants

Reaction Steps

To a solution of 26.6 g (0.02 m) of tetrahydroquinoline in 50 ml of pyridine, cooled to 0° C., there were added 28.1 g (0.02 m) of benzoyl chloride dropwise and with stirring at a rate such the temperature was kept below -5° C. After addition was complete, the mixture was stirred at room temperature for 1 hour and then poured into a separatory funnel containing 500 ml of water and 50 ml of conc. hydrochloric acid. Ethyl ether (300 ml) was added to the funnel and the mixture shaken until all of the precipitated oil had dissolved in the ether. After washing with water, the ether layer was filtered through anhydrous calcium sulfate and evaporated to a volume of about 150 ml. Petroleum ether (100 ml) was added to the solution which was then cooled in a refrigerator to give 35.7 g (75% yield) of 1-benzoyltetrahydroquinoline as colorless crystals, m.p. 80°-81° C.

Provenance & Evidence