Acetic Acid → 4-Benzylidenehomophthalimide

HRID 432671Notes

Reaction equation

HRID 432671 reaction equation
[C:1]1(=[O:12])[NH:6][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1CCCCC1.C(O)(=O)C>O>[CH:13](=[C:9]1[CH:10]=[CH:11][C:3]2[CH2:2][C:1]([NH:6][C:5](=[O:7])[C:4]=2[CH2:8]1)=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8082PiperidineHCID 3494351,3(2H,4H)-isoquinolinedione

Product 1

HCID 1317242574-BenzylidenehomophthalimideYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of homophthalimide (15 g, 93 mmol), benzaldehyde (9.9 g, 93 mmol), piperidine (9 ml) and acetic acid (465 ml) was heated under reflux for 1 hour, cooled to ambient temperature and diluted with water (500 ml). The resulting solid was collected by filtration, washed with water and dried in vacuo to give 4-benzylidenehomophthalimide (18.5 g, 82%) as a solid; m.pt. 173-177° C. Used crude for the next step.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-3ed1c6bb572346d38519790eb429ae25
Source dataset
uspto-grants-2003_12
Patent number
US06664269B2

Reaction notes

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