Water → 4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-phthalic Acid Dimethyl Ester

HRID 2080726Notes

Reaction equation

HRID 2080726 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].Br[N:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:23].N([C:31]([CH3:35])([CH3:34])C#N)=NC(C)(C)C#N.O.[C:37](Cl)(Cl)(Cl)Cl>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[CH:10][C:11]([CH2:14][N:17]2[C:21](=[O:22])[C:20]3[C:19](=[CH:37][CH:35]=[CH:31][CH:34]=3)[C:18]2=[O:23])=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 5

HCID 962WaterHCID 5943Carbon Tetrachloride2×HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 88370Dimethyl 4-methylphthalate

Product 1

HCID 669417474-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-phthalic Acid Dimethyl Ester

Procedure

The compound (202 mg) obtained in Example 7-1 was dissolved in carbon tetrachloride (7.1 ml) and added with N-bromosuccinimide (205 mg) and 2,2′-azobisisobutyronitrile (15.8 mg) and the whole was refluxed under heating for 20 hours. The solution was further added with carbon tetrachloride (7.0 ml) and N-bromosuccinimide (51.3 mg) and the whole was refluxed under heating for additional 4 hours. After having been left for cooling, the solution was added with water to stop the reaction and then subjected to extraction with chloroform. The organic layer was washed with water and a saturated saline solution and then dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then dissolved in DMF (5.8 ml) The solution was added with potassium phthalimide (359 mg) and stirred at room temperature for 16 hours. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (226 mg) as a white solid.

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 20 hours
  3. temperaturethe whole was refluxed
  4. temperatureunder heating for additional 4 hours
  5. waitAfter having been left
  6. temperaturefor cooling
  7. customthe reaction
  8. extractionsubjected to extraction with chloroform
  9. washThe organic layer was washed with water
  10. dry with materiala saturated saline solution and then dried with anhydrous sodium sulfate
  11. distillationThe solvent was distilled off
  12. dissolutionthe residue was then dissolved in DMF (5.8 ml) The solution
  13. additionwas added with potassium phthalimide (359 mg)
  14. customThe residue obtained
  15. distillationby distilling the solvent
  16. customoff was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-66ab256b8f09470d859f8c2c45cc3b2c
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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