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

HRID 1701278Notes

Reaction equation

HRID 1701278 reaction equation
N[C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10]#[N:11].C(O)C[OH:18].[OH-].[K+]>O>[CH:7]1[CH:8]=[CH:9][N:5]2[CH2:4][C:3]3[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=3[NH:11][C:10](=[O:18])[C:6]=12

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 14856621-(2-Aminobenzyl)-1H-pyrrole-2-carbonitrile

Product 1

HCID 4682545,10-Dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. additionA mixture of 10 g
  2. temperaturecooled
  3. additiondiluted with 100 ml
  4. filtrationThe crystals which form are collected by filtration
  5. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-6a932b4384124d27877eed007e896817
Source dataset
uspto-grants-1980_03
Patent number
US04192803

Reaction notes

Loading…