Phthalic Anhydride → 2-[2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dione

HRID 2211710

Reaction equation

HRID 2211710 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][C:13]1([CH3:33])[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[C:16]2[C:25]([CH3:32])=[C:26]([NH2:31])[C:27]([CH3:30])=[C:28]([CH3:29])[C:15]=2[O:14]1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.[OH-].[Na+]>O1CCCC1>[CH3:12][C:13]1([CH3:33])[CH:17]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[C:16]2[C:25]([CH3:32])=[C:26]([N:31]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])[C:27]([CH3:30])=[C:28]([CH3:29])[C:15]=2[O:14]1

Participants

7

Reactant 5

HCID 6811Phthalic AnhydrideHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 106853092,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

Product 1

HCID 219613242-[2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dioneYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of phthalic anhydride (566.4 mg, 3.82 mmol) in tetrahydrofuran (5 ml) was added a solution of 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine (987.3 mg, 3.38 mmol) in tetrahydrofuran(10 ml) and the resulting mixture was refluxed with heating for 11 hours. The reaction mixture was cooled down to room temperature and then concentrated under reduced pressure. Sodium acetate (314.6 mg, 3.84 mmol) and acetic anhydride (20 ml) were added into the residue and the resulting mixture was stirred at 90° C. for 2 hours. The reaction mixture was cooled down to room temperature and then an 8 N aqueous solution of sodium hydroxide was added into the mixture until it became basic. The product was extracted twice with ethyl acetate. The combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from ethyl acetate to obtain 1.16 g (81% yield) of the title compound. Melting point: 222-224° C.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. temperaturewith heating for 11 hours
  3. concentrationconcentrated under reduced pressure
  4. temperatureThe reaction mixture was cooled down to room temperature
  5. extractionThe product was extracted twice with ethyl acetate
  6. washThe combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate
  7. customdried on magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-8a40d6a9621d4d11bf60eb084d5af384
Source dataset
uspto-grants-2006_09
Patent number
US07101867B2

Linked notes

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