Epichlorohydrin → HCID 13187649, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6.6 g of 4-phenyl-1(2H)-isoquinolone, 2.9 g of 50% sodium hydride and 80 ml of dimethylformamide was stirred at 60° to 70° C. for 3 hours. 5.5 g of epichlorohydrin was then added dropwise to the reaction solution while cooling and stirring, and the mixture was then stirred at room temperature for 12 hours. The reaction solution was poured into ice-water, and the precipitated crystals were collected by filtration and washed with water. The crystals thus obtained were dissolved in 40 ml of dimethylformamide, 12 ml of diethylamine was added thereto and the mixture was heated at 100° C. for 5 hours in a sealed tube. The residue obtained after distilling off the solvent was dissolved in diethyl ether, and the solution was washed with water and extracted with 5% hydrochloric acid. The extract was rendered neutral with 10% aqueous solution of sodium hydroxide to precipitate crystals which were then collected by filtration and recrystallized from a mixture of ethyl acetate and petroleum ether to obtain 6.5 g (61% yield) of 2-(3-diethylamino-2-hydroxypropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 106° C. as colorless prisms.

Provenance & Evidence