Ethyl Acetate → HCID 13827276, compound

Participants

Reaction Steps

A solution of 27.5 gm of trans-6-[2-(4-hydroxyphenyl)ethenyl]-1-(2H)-phthalazinone (as prepared in Example 2) in 1300 ml DMSO was treated with 135 ml 2.5N sodium hydroxide solution, followed by 12.5 ml n-butyl iodide. The reaction mixture was stirred for 21/2 hours, then added to 8000 ml ethyl acetate. After stirring for a few minutes the insoluble material was filtered off and washed with a little ethyl acetate. The ethyl acetate was removed on a rotary evaporator and the residue added to 8000 ml water, stirred for an hour and allowed to settle overnight. The clear supernatant liquid was syphoned off and the residual slurry was filtered and the crude product washed thoroughly with water. After air drying it weighed 24.8 gm. The crude product was recrystallized from 125 ml 2-methoxyethanol, filtered and washed with isopropanol and ether. After drying at 60° for 24 hours, it weighed 17.4 gm and melted at 225°-230° C.

Provenance & Evidence