2-Methoxyethanol → 2-Pyrrolidinone, 1-(8-quinolinyl)-

Participants

Reaction Steps

8-Aminoquinoline (2.0 g, 13.9 mmol) and 4-bromobutyronitrile (2.0 g, 13.9 mmol) were refluxed in 2-methoxyethanol (20 ml) for 24 hours under a nitrogen atmosphere. A few drops of water were added to hydrolyze the 1-(8-quinolyl)-2-iminopyrrolidinone produced, and the mixture was evaporated under vacuum. The residual oil was triturated with diethyl ether (50 ml) and decanted. Upon standing at ambient temperature the ether solution deposited 0.65 g of 1-(8-quinolyl)-2-pyrrolidinone, (m.p. 119°-121°). The ether insoluble oil was dissolved in acetone, filtered and combined with the ether liquor. The solvents were evaporated; the residue was dissolved in methylene chloride, washed with 30% aqueous sodium hydroxide and with water. The water layer was back-extracted with methylene chloride, and the combined methylene chloride layers were dried, filtered, and evaporated. The semi-solid residue was triturated with ether and the mixture filtered to yield 0.40 g of 1-(8-quinolyl)-2-pyrrolidinone, (m.p. 118°-120°). The ether mother-liquor upon standing gave a second crop of 0.50 g, (m.p. 119°-120°). The combined yield was 1.55 g or 52%.

Provenance & Evidence