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

HRID 1902828Notes

Reaction equation

HRID 1902828 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Br[CH2:13][CH2:14][CH2:15][C:16]#N.C[O:19]CCO>O>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[N:1]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:19])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 113598-AminoquinolineHCID 214124-Bromobutyronitrile

Product 1

HCID 30614652-Pyrrolidinone, 1-(8-quinolinyl)-

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

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%.

Workup

  1. customproduced
  2. customthe mixture was evaporated under vacuum
  3. customThe residual oil was triturated with diethyl ether (50 ml)
  4. customdecanted
  5. customUpon standing at ambient temperature
  6. dissolutionThe ether insoluble oil was dissolved in acetone
  7. filtrationfiltered
  8. customThe solvents were evaporated
  9. dissolutionthe residue was dissolved in methylene chloride
  10. washwashed with 30% aqueous sodium hydroxide and with water
  11. extractionThe water layer was back-extracted with methylene chloride
  12. dry with materialthe combined methylene chloride layers were dried
  13. filtrationfiltered
  14. customevaporated
  15. customThe semi-solid residue was triturated with ether
  16. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-b81ac7a244f04e28853c956f85d5c503
Source dataset
uspto-grants-1982_12
Patent number
US04366158

Reaction notes

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