Gamma-Butyrolactone → 2-Pyrrolidinone, 1-(8-quinolinyl)-

HRID 1902822

Reaction equation

HRID 1902822 reaction equation
[H-].[K+].[NH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2.[C:14]1(=O)[O:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[N:12]1[C:13]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]2[CH2:14][CH2:15][CH2:16][C:17]2=[O:18])[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 7302Gamma-ButyrolactoneHCID 73974-Toluenesulfonyl chlorideHCID 113598-AminoquinolineHCID 82127Potassium hydride

Product 1

HCID 30614652-Pyrrolidinone, 1-(8-quinolinyl)-Yield 5.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent4×HCID 12679HexamethylphosphoramideSolvent

Procedure

Potassium hydride in oil was washed with dry pentane (in a dry nitrogen atmosphere) leaving 2.5 g (0.062 mole) of potassium hydride which was covered with dry tetrahydrofuran (25 ml). To the slurry of potassium hydride (at room temperature) was added dropwise a solution of 8-aminoquinoline (5 g, 0.035 mole) in dry tetrahydrofuran (25 ml), with stirring, followed by addition of dry hexamethylphosphoric triamide (25 ml). After stirring for 1 hour at room temperature, the reaction was cooled in an ice bath and a solution of γ-butyrolactone (2.8 ml, 0.036 mole) in dry tetrahydrofuran (10 ml) was added and the reaction stirred for 1 hour. The reaction was warmed to room temperature and a solution of p-toluenesulphonyl chloride (8 g, 0.042 mole) in dry tetrahydrofuran (10 ml) was added. The reaction was poured into ice water, filtered and the pH was adjusrted to pH 3.5. The product was extracted with methylene chloride and washed with cupric chloride to remove traces of 8-aminoquinoline. The product organics were dried, concentrated under reduced pressure and the residue was crystallized from ether/pentane affording 1-(8-quinolyl)-2-pyrrolidinone, yield 5.4%, which was identical by tlc and NMR in comparison with the product of Example 1.

Workup

  1. stirringAfter stirring for 1 hour at room temperature
  2. temperaturethe reaction was cooled in an ice bath
  3. stirringthe reaction stirred for 1 hour
  4. filtrationfiltered
  5. extractionThe product was extracted with methylene chloride
  6. washwashed with cupric chloride
  7. customto remove traces of 8-aminoquinoline
  8. customThe product organics were dried
  9. concentrationconcentrated under reduced pressure
  10. customthe residue was crystallized from ether/pentane

Sources & evidence

ORD record
ord-14b0d5e7ee5848febb35f0528de94534
Source dataset
uspto-grants-1982_12
Patent number
US04366158

Linked notes

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