HCID 18924794, compound → 2-(4-Nitro-benzyl)-isoindole-1,3-dione

HRID 1428707Notes

Reaction equation

HRID 1428707 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)(=O)=O.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C)C=O>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][N:20]2[C:16](=[O:26])[C:17]3[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:19]2=[O:21])=[CH:8][CH:9]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 18924794HCID 18924794, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 2708672-(4-Nitro-benzyl)-isoindole-1,3-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-nitrobenzyl methanesulfonate (2.2 g, 9.51 mmol) in dimethylformamide (10 mL) was added potassium phthalimide (1.9 g, 10.5 mmol) and stirred at room temperature for overnight. TLC showed complete consumption of starting material. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by crystallization to give 2-(4-nitrobenzyl)isoindoline-1,3-dione (1.6 g, 60%).

Workup

  1. customconsumption of starting material
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by crystallization

Sources & evidence

ORD record
ord-b6e5feea614c435fb97bf2b69690d100
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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