Sodium Hydroxide → 2-[3-(3-Cyanopropoxy)phenoxymethyl]quinoline

Participants

Reaction Steps

A mixture of 15.3 g of 2-chloromethylquinoline hydrochloride, 12.6 g of 4-(3-hydroxyphenoxy)butyronitrile and 5.7 g of sodium hydroxide was stirred with 80 ml of dimethylsulfoxide at room temperature for 4 hours. The reaction mixture was partitioned between water and ether. The ether extract was evaporated to yield 23.9 g, of crude product. Crystallization from ethyl acetate:hexane and then from ethanol:hexane gave 15 g of grey needles, m.p. 84°-85° C.

Provenance & Evidence