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

HRID 1902827Notes

Reaction equation

HRID 1902827 reaction equation
[C:1]1(=[O:6])O[CH2:4][CH2:3][CH2:2]1.[NH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2>[Cl-].[Zn+2].[Cl-]>[N:16]1[C:17]2[C:12](=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]2[CH2:4][CH2:3][CH2:2][C:1]2=[O:6])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 7302Gamma-ButyrolactoneHCID 113598-Aminoquinoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of γ-butyrolactone (4.3 g), 8-aminoquinoline (7.2 g) and zinc chloride (0.7 g) was heated at 225° for 20 hours in an autoclave. The cooled reaction mixture was partitioned between chloroform and 0.2 N hydrochloric acid. The aqueous layer was basified with sodium hydroxide then extracted with methylene chloride. Following treatment of the methylene chloride extract with FILTROL No. 1 (Trade Name) the solvent was vacuum-stripped to give 1-(8-quinolyl)-2-pyrrolidinone, identical by tlc with the product of Example 1.

Workup

  1. temperaturewas heated at 225° for 20 hours in an autoclave
  2. customThe cooled reaction mixture
  3. customwas partitioned between chloroform and 0.2 N hydrochloric acid
  4. extractionthen extracted with methylene chloride
  5. extractionextract with FILTROL No

Sources & evidence

ORD record
ord-a316e2e0eac340348898642f605d0b84
Source dataset
uspto-grants-1982_12
Patent number
US04366158

Reaction notes

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