Sodium Hydroxide → 1-(3-Chloro-alpha,alpha-dimethylbenzyl)-4-methyl-3-phenyl-3-pyrrolin-2-one

HRID 1461655Notes

Reaction equation

HRID 1461655 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([N:8]([CH2:18][C:19](=O)[CH3:20])[C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:7])[CH3:6].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([N:8]1[CH2:18][C:19]([CH3:20])=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]1=[O:17])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15754160N-(3-chloro-alpha,alpha-dimethylbenzyl)-N-(2-oxopropyl)phenylacetamide

Product 1

HCID 157541671-(3-Chloro-alpha,alpha-dimethylbenzyl)-4-methyl-3-phenyl-3-pyrrolin-2-oneYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

34.4 g (0.1 mol) of N-(3-chloro-α,α-dimethylbenzyl)-N-(2-oxopropyl)phenylacetamide prepared in accordance with the method of Reference Example 6, was dissolved in 200 ml of ethanol, and 0.5 (0.009 mol) of sodium hydroxide powder was added thereto. The mixture was refluxed under heating for 10 minutes. Then, the solvent was distilled off under reduced pressure, and then water was added thereto. The mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 21.2 g (yield: 65.2%) of the desired compound.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 10 minutes
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customfollowed by purification by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9532379227944b01aec33b33312a425c
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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