Water → 2-(2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1957099Notes

Reaction equation

HRID 1957099 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].O.[CH3:14][N:15](C)[CH:16]=[O:17]>>[C:1]1(=[O:11])[N:5]([CH:1]2[CH2:2][CH2:10][C:9]3[CH:8]=[CH:7][CH:3]=[CH:4][C:14]=3[NH:15][C:16]2=[O:17])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 3

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24194345Phthalimide potassium salt

Product 1

HCID 140106802-(2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Conditions

Temperature
60 °C

Procedure

80 g of the product which was obtained above were suspended in 140 ml of dimethylformamide. A solution of 72.6 g of potassium phthalimide in 205 ml of dimethylformamide was added to the suspension and the mixture was then stirred at 60° C. for 16 hours. For the working-up, it was cooled down to room temperature and 800 ml of water were slowly added dropwise; the mixture was then stirred for 2 hours while cooling with ice. The resulting crystal slurry was filtered out with suction, washed firstly with a water/dimethylformamide mixture and then with methyl tert-butyl ether, and subsequently dried at 60° C. for 2 days under reduced pressure. 73.3 g of 4,5-dihydro-3-phthalimido-1H-1-benzazepin-2 (3H) -one were obtained with a melting range of from 185° to 195° C.

Workup

  1. temperatureit was cooled down to room temperature
  2. stirringthe mixture was then stirred for 2 hours
  3. temperaturewhile cooling with ice
  4. filtrationThe resulting crystal slurry was filtered out with suction
  5. washwashed firstly with a water/dimethylformamide mixture
  6. dry with materialwith methyl tert-butyl ether, and subsequently dried at 60° C. for 2 days under reduced pressure

Sources & evidence

ORD record
ord-151b3883a81a4ffd90d6f9f05a2052eb
Source dataset
uspto-grants-1998_07
Patent number
US05783573

Reaction notes

Loading…