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

HRID 1902826Notes

Reaction equation

HRID 1902826 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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C>[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

5

Reactant 3

HCID 7302Gamma-Butyrolactone2×HCID 113598-AminoquinolineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of γ-butyrolactone (9.5 g), technical grade 8-aminoquinoline (14.4 g), p-toluenesulphonic acid monohydrate (1.90 g) and mixed xylenes (15 ml) were refluxed with a Dean Stark trap prefilled with xylenes. After one hour γ-butyrolactone (9.0 g) was added and reflux was resumed for two hours. The residue obtained by concentration by vacuum distillation (≃15 mm Hg) of the reaction mixture was extracted with hot ethyl acetate (100 ml). The solid which formed upon cooling the ethyl acetate solution was recrystallized from acetone giving 1-(8-quinolyl)-2-pyrrolidinone, (m.p. 119°-123°), identical by tlc with the product of Example 1.

Workup

  1. temperaturewere refluxed with a Dean Stark trap
  2. temperaturereflux
  3. customThe residue obtained by concentration by vacuum distillation (≃15 mm Hg) of the reaction mixture
  4. extractionwas extracted with hot ethyl acetate (100 ml)
  5. customThe solid which formed
  6. customwas recrystallized from acetone

Sources & evidence

ORD record
ord-98f2a5856291492e85077cbfd3de90d1
Source dataset
uspto-grants-1982_12
Patent number
US04366158

Reaction notes

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