Epichlorohydrin → HCID 20360753, compound

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Reaction Steps

A mixture of finely powdered 6-(3-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (21.6 g, 0.11 mole), epichlorohydrin (90 ml, 1.1 mole), and piperidine (1 ml) was heated on a steam bath for 90 minutes. Evaporation of the solution under reduced pressure gave an oil which was dissolved in dichloromethane and stirred with dilute sodium hydroxide solution (60 ml). The organic phase was washed with water, dried, and evaporated under reduced pressure to a viscous oil (27 g, 96%). Purification on a silica column by eultion with chloroform gave 6-[3-(2,3-epoxypropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone (16.5 g, 59%) as an oil which, when treated with ether, gave a white solid (13.7 g, 49%, m.p. 108°-112° C). The pure epoxide, recrystallised from methanol-petroleum ether (b.p. 60°-80° C), had m.p. 110°-112° C. (Found: C, 63.96; H, 5.70; N, 11.43; M+ , 246. C13H14N2O3 requires: C, 63.39; H, 5.73; N, 11.38%; M, 246).

Provenance & Evidence