Water → 3-((1,3-Dioxoisoindolin-2-yl)methyl)benzonitrile

HRID 1734017Notes

Reaction equation

HRID 1734017 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl)#[N:2].[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K].O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][N:15]1[C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]2[C:11]1=[O:21])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5221263-(Chloromethyl)benzonitrileHCID 24194345Phthalimide potassium salt

Product 1

HCID 123753363-((1,3-Dioxoisoindolin-2-yl)methyl)benzonitrileYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-cyanobenzyl chloride (13.3 g) in N,N-dimethylformamide (30 ml) was added dropwise to a suspension of potassium phthalimide (15.9 g) in N,N-dimethylformamide (160 ml) at ambient temperature under stirring and the resultant mixture was stirred for 12 hours at ambient temperature. The reaction mixture was poured into water and the precipitate was collected by filtration. The precipitate was dissolved in a mixture of ethyl acetate and tetrahydrofuran and the resultant solution was washed with brine and dried over magnesium sulfate. The solvent was concentrated in vacuo and the precipitate was collected by filtration to give N-(3-cyanobenzyl)phthalimide (17.1 g).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. dissolutionThe precipitate was dissolved in a mixture of ethyl acetate and tetrahydrofuran
  3. washthe resultant solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solvent was concentrated in vacuo
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c2f4a0c0420e4d458ec5288de8bd9524
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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