Sodium Hydroxide → 2-Pyrrolidinone, 1-(8-quinolinyl)-

HRID 1902824Notes

Reaction equation

HRID 1902824 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH: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:6].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[N:16]1[C:17]2[C:12](=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 128985464-chloro-N-(8-quinolyl)butyramide

Product 1

HCID 30614652-Pyrrolidinone, 1-(8-quinolinyl)-Yield 90%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chloro-N-(8-quinolyl)butyramide (2.5 g, 0.01 mole) and benzyltriethyl ammonium chloride (0.115 g, 5 mole%) in methylene chloride (30 ml) was stirred at room temperature. A solution of 30% aqueous sodium hydroxide (10 ml) was added and the mixture was stirred for 16 hours. The reaction mixture was then diluted with methylene chloride, the organic layer was drawn off and washed with a saturated salt solution, dried over sodium sulphate and evaporated to a solid residue. The residue was recrystallized from methylene chloride/petroleum ether to afford 1-(8-quinolyl)-2-pyrrolidinone which was identical by tlc and NMR in comparison with the product of Example 1, yield 90%.

Workup

  1. washwashed with a saturated salt solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated to a solid residue
  4. customThe residue was recrystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-5e46261967d34ef6bd36697eb14215cf
Source dataset
uspto-grants-1982_12
Patent number
US04366158

Reaction notes

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