Ethylene Glycol → HCID 19095275, compound

Participants

Reaction Steps

N-[2-(2-Phenylpyrrol-1-yl)ethyl]acetamide (0.9 g) and 5 ml of ethylene glycol was added in succession to a solution of 1.0 g of potassium hydroxide in 10 ml of water. The reaction mixture was stirred at the boiling point for 24 hours. The cold mixture was extracted twice with 50 ml of methylene chloride each time, the organic phases were combined and extracted twice with 50 ml of 2N hydrochloric acid each time. The aqueous phases were combined, brought to a pH value of 12 by the addition of 28% sodium hydroxide solution and again extracted twice with 50 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. 0.3 g of a total of 0.6 g of crude product were dissolved in a 20-fold amount of ethanol and treated with 2 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.3 g (64%) of 1-(2-aminoethyl)-2-phenylpyrrole fumarate (1:1); m.pt.: 169°-171° C.

Provenance & Evidence