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

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

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.