2-Nitrobenzyl chloride → 2-[(2-nitrophenyl)methyl]isoindole-1,3-dione

HRID 1902191

Reaction equation

HRID 1902191 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([N-:9][C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].[K+].[N+:13]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Cl)([O-:15])=[O:14]>CN(C)C=O>[N+:13]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][N:9]1[C:7](=[O:8])[C:5]2=[CH:6][CH:1]=[CH:2][CH:3]=[C:4]2[C:10]1=[O:11])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 119212-Nitrobenzyl chlorideHCID 3356745Potassium phthalimide

Product 1

HCID 3195372-[(2-nitrophenyl)methyl]isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 54.0 of N-potassium phthalimide, 50.0 g of o-nitrobenzyl chloride and 120 ml of dimethylformamide is refluxed for 3 hours and poured into 900 ml of ice-water while stirring. After 30 minutes, it is filtered, and the residue washed with water, to yield the N-o-nitrobenzyl-phthalimide melting at 190°-209°.

Workup

  1. temperatureis refluxed for 3 hours
  2. filtrationit is filtered
  3. washthe residue washed with water

Sources & evidence

ORD record
ord-eead5c0713aa4ff4979b78921b536494
Source dataset
uspto-grants-1982_12
Patent number
US04362666

Linked notes

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