504-30-3

110-89-4

60-29-7

106-89-8

56872-17-4

504-30-3

56872-18-5

III. A finely ground mixture of 6-(3-allyl-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (50 g, 0.22 mol), epichlorohydrin (200 g, 2.2 mol) and piperidine (2 g) was heated on a steam bath for 90 minutes. Upon completion of the reaction, the volatile components were removed by evaporation under reduced pressure to give a viscous oily substance. The oily substance was dissolved in dichloromethane and subsequently washed with dilute sodium hydroxide solution (500 mL) with agitation for 10 minutes. The organic phase was separated, washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain the oily substance, which gradually solidified during standing. Addition of ethanol ether to the solid afforded 6-[3-allyl-4-(2,3-epoxypropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone (30 g, 47% yield, melting point 92.5°-95°C). The pure pyridazinone (melting point 93.5°-95°C) was further obtained by recrystallization from aqueous ethanol. The results of the elemental analyses were as follows: measured values (C, 67.41; H, 6.47; N, 9.80; M+, 286), which are in agreement with the theoretical values (C16H18N2O3: C, 67.11; H, 6.33; N, 9.79; M, 286).