Phthalic Anhydride → 2-[3-(Dimethylamino)propyl]-1H-isoindole-1,3(2H)-dione
Reaction equation
F[B-](F)(F)F.[C:6]1(=[O:23])[N:10]([CH2:11][CH2:12][CH2:13][N+:14](C)([CH3:16])[CH3:15])[C:9](=[O:18])[C:8]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:7]12.CN(C=CC)C.C(N(CC)CC)C.C1(=O)OC(=O)C2=CC=CC=C12>C1(C)C(C)=CC=CC=1>[CH3:15][N:14]([CH2:13][CH2:12][CH2:11][N:10]1[C:9](=[O:18])[C:8]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:7]2[C:6]1=[O:23])[CH3:16]Participants
Procedure
There was prepared (3-phthalimidopropyl)trimethylammonium tetrafluoroborate by dissolving 145 grams, 1.42 moles, of dimethylaminopropylene, and 3.92 grams, 0.039 moles of triethylamine in one liter of xylene, in a two litered three necked round bottom flask equipped with a stirrer, a thermometer, a heating mantle, a Dean-Stark trap, and a reflux condenser. Subsequently 191.3 grams, 1.29 moles of phthalic anhydride was added, and the mixture was refluxed at a temperature of 140 degrees centigrade. Subsequent to refluxing for 24 hours, 24 milliliters of water was collected in the Dean-Stark trap. The xylene and excess amines were then removed from the reaction mixture on a rotary evaporator yielding the crude product N-(dimethylaminopropyl)phthalimide, in a yield of 300 grams. The crude imide separated was a brown syrup which crystallized on standing. This imide product, subsequent to purification by vacuum distillation, was identified by elemental analysis and infrared spectroscopy.
Workup
- dissolutionby dissolving 145 grams, 1.42 moles
- temperaturethe mixture was refluxed at a temperature of 140 degrees centigrade
- temperatureSubsequent to refluxing for 24 hours
- custom24 milliliters of water was collected in the Dean-Stark trap
- customThe xylene and excess amines were then removed from the reaction mixture on a rotary evaporator
Sources & evidence
- ORD record
- ord-da799152df1d4a13bc257db9aec15479
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04493883
Reaction notes
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