Hydrogen Peroxide → 3-[4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide

HRID 1727159Notes

Reaction equation

HRID 1727159 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][N:18]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]#[N:24])[C:17](=[O:28])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].OO.[OH:33]S(O)(=O)=O>C(O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][N:18]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]([NH2:24])=[O:33])[C:17](=[O:28])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 104746693-[4-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile

Product 1

HCID 99525243-[4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamideYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 12.5 mg of benzonitrile 42 (0.033 mmol) in 0.5 mL of ethanol was added 2 μL of a 25% NaOH solution followed by 29 μL of 35% H2O2. The temperature of the reaction mixture was kept at 50° C. for 3 h. Upon completion, 5% H2SO4 was added until the mixture was neutral (pH 7). The reaction mixture was extracted with EtOAc and dried with MgSO4. Concentration and purification of the residue by column chromatography on silica gel gave the desired product as a white solid. Yield: 94%.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialdried with MgSO4
  3. concentrationConcentration and purification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-44a298f8c48148c9afa965841923487c
Source dataset
uspto-grants-2009_02
Patent number
US07495016B2

Reaction notes

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