5-Chloro-8-hydroxyquinoline → HCID 18968588, compound

Participants

Reaction Steps

10.0 mmol of 5-chloro-8-hydroxyquinoline (ALDRICH) are dissolved, with stirring, in 20 ml of dry DMF, in a 50 ml round-bottomed flask provided with stirring and a thermometer. Then 11 mmol of potassium carbonate and 10% by weight of potassium iodide are added. A solution of 11 mmol of benzyl chloride (JANSSEN) in 5 ml of DMF is added dropwise over 5 minutes, at room temperature and with stirring. After 18 hours of reaction at 50° C., the reaction mixture, supplemented with 100 ml of water is extracted with 4×50 ml of tert-butyl methyl ether. The organic phases are combined, then washed with 3×50 ml of 1N HCl. The aqueous phases are combined, alkalized to pH=9 and extracted with 2×50 ml of ethyl acetate. After drying the organic phase over MgSO4, the solvent is evaporated under reduced pressure. The desired product is obtained after recrystallization from ethanol.

Provenance & Evidence