Water → HCID 21533397, compound

Participants

Reaction Steps

14 g of 3-carboethoxy-4-hydroxy-6-cyclohexyl-quinoline are added to a solution of 1.45 g of sodium in 150 ml of absolute methanol, whilst stirring, and the mixture is heated to the boil for 1 hour, with exclusion of water. 7.15 g of benzyl chloride are then added dropwise to the reaction mixture, which is boiled for a further 5 hours under reflux. It is then evaporated to dryness in vacuo and the residue is partitioned between 4 times 500 ml of chloroform and 500 ml of 1 N potassium hydroxide solution at 0°C. The organic phases are washed with twice 500 ml of water, dried over sodium sulphate and evaporated to dryness in vacuo. Repeated crystallisation of the evaporation residue from ethanol gives 1-benzyl-3-carbomethoxy-4-oxo-6-cyclohexyl-1,4-dihydroquinoline of melting point 211°-213°C.

Provenance & Evidence