Dimethylformamide → 2-(4-Nitro-benzyl)-isoindole-1,3-dione

HRID 1356930Notes

Reaction equation

HRID 1356930 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6809PhthalimideHCID 74824-Nitrobenzyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 2708672-(4-Nitro-benzyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of phthalimide (4 g), p-nitrophenylmethylchloride (4,7 g), potassium carbonate (4 g) and DMF (20 ml) was stirred at 150° C. for 1.5 h. After cooling, the mixture was diluted with water. The precipitate was filtered and the crude product (I) was recrystallized from ethanol.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered
  3. customthe crude product (I) was recrystallized from ethanol

Sources & evidence

ORD record
ord-d5a40e506e1e4b02b500500ace994495
Source dataset
uspto-grants-2003_07
Patent number
US06589452B2

Reaction notes

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