Reaction #72711

Reaction equation

phthalic anhydride

N,N-dimethyl hydrazine dihydrochloride

diethyl-phenyl-amine

→

desired product

Yield 85.0%

2-Dimethylamino-isoindole-1,3-dione

Yield 85.0%

Solvents

toluene

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   TemperatureThe reaction mixture was refluxed for 18 hours
3. 3
   Otherwhile removing the formed water via a Dean-Stark trap
4. 4
   OtherThen, toluene was evaporated under reduced pressure
5. 5
   Otherthe resulting crude was purified on silica gel chromatography with (1:5) EtOAc

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.

Source