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

HRID 1174028Notes

Reaction equation

HRID 1174028 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 129-1 was dissolved in carbon tetrachloride (7.1 ml) and added with N-bromosuccinimide (205 mg) and azobisisobutyronitrile (15.8 mg), followed by thermal reflux for 20 hours. The solution was further added with carbon tetrachloride (7.0 ml) and N-bromosuccinimide (51.3 mg), followed by thermal reflux for 4 hours. After having been stood to cool, the solution was added with water and then subjected to extraction with chloroform. The organic layer was washed with water and 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. temperatureby thermal reflux for 20 hours
  2. temperatureby thermal reflux for 4 hours
  3. temperatureto cool
  4. extractionsubjected to extraction with chloroform
  5. washThe organic layer was washed with water and saturated saline solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. dissolutionthe residue was then dissolved in DMF (5.8 ml)
  9. additionThe solution was added with potassium phthalimide (359 mg)
  10. customThe residue obtained
  11. distillationby distilling the solvent
  12. customoff was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c7a21590eb004b7ab589aa70a70e4728
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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