Ethylene Glycol → 5,10-Dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one

Participants

Reaction Steps

A mixture of 10 g. of 1-(o-aminobenzyl)-2-pyrrolecarbonitrile [M. Artico et al., I1 Farmaco Ed. Sci., 24 (11), 980 (1969)], 60 ml. of ethylene glycol and 8 g. of 85% potassium hydroxide is heated in an oil bath at 180° C. for 2 hours, cooled and then diluted with 100 ml. of water. The crystals which form are collected by filtration and recrystallized from 95% ethanol, giving pure 5,10-dihydro-11H-pyrrolo[2,1-c][1,4]-benzodiazepin-11-one. The aqueous mother liquor, when treated with acetic acid to pH 4-5, gives 1-o-aminobenzyl-2-pyrrolecarboxylic acid.

Provenance & Evidence