Phthalic Anhydride → 2-(Dimethylamino)isoindoline-1,3-dione

HRID 44433

Reaction equation

HRID 44433 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.Cl.Cl.[CH3:14][N:15]([CH3:17])[NH2:16].C(N(CC)C1C=CC=CC=1)C>C1(C)C=CC=CC=1>[CH3:14][N:15]([CH3:17])[N:16]1[C:4](=[O:5])[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1]1=[O:6]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 7061N,N-DiethylanilineHCID 30169721,1-Dimethylhydrazine dihydrochloride

Product 1

HCID 2489762-(Dimethylamino)isoindoline-1,3-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the suspension of phthalic anhydride (62.5 mmol) in toluene (500 ml), N,N-dimethyl hydrazine dihydrochloride (50 mmol) and diethyl-phenyl-amine (90 mmol) were added. The reaction mixture was refluxed for 18 hours while removing the formed water via a Dean-Stark trap. Then, toluene was evaporated under reduced pressure and the resulting crude was purified on silica gel chromatography with (1:5) EtOAc:dichloromethane, to give the desired product in 85% yield.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for 18 hours
  3. customwhile removing the formed water via a Dean-Stark trap
  4. customThen, toluene was evaporated under reduced pressure
  5. customthe resulting crude was purified on silica gel chromatography with (1:5) EtOAc

Sources & evidence

ORD record
ord-9556816542c64a74867182946ad62c50
Source dataset
uspto-grants-2013_09
Patent number
US08541428B2

Linked notes

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