Water → 2-[2-(4-Chloro-phenyl)-cyclopropyl]-isoindole-1,3-dione

HRID 1916024Notes

Reaction equation

HRID 1916024 reaction equation
[Na].S(NN=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)(C1C=CC(C)=CC=1)(=O)=O.[CH:22]([N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])=[CH2:23].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH:14]2[CH2:23][CH:22]2[N:24]2[C:25](=[O:34])[C:26]3[C:27](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:29])=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 962WaterHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 866384034-Chlorobenzaldehyde tosyl hydrazone sodium salt

Product 1

HCID 684102072-[2-(4-Chloro-phenyl)-cyclopropyl]-isoindole-1,3-dioneYield 26.3%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 168478Rhodium acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chlorobenzaldehyde tosyl hydrazone sodium salt (1.67 g, 5.05 mmol), benzyltriethylammoniumchloride (115 mg, 0.5 mmol), rhodium acetate (20 mg, 0.05 mmol) and N-vinylphtalimide (4.32 g, 25.0 mmol) in dry 1,4-dioxane (13 ml) was stirred for one day under nitrogen at room temperature. Water (35 ml) was added to the mixture and the aqueous phase was extracted three times with dichloromethane. The combined organic layers were dried over Na2SO4. Evaporation gave the crude material, which was purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 1:1). To afford 392 mg (26.3% of theory) of 2-[2-(4-chloro-phenyl)-cyclopropyl]-isoindole-1,3-dione in the form of a solid.

Workup

  1. extractionthe aqueous phase was extracted three times with dichloromethane
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customEvaporation
  4. customgave the crude material, which
  5. customwas purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 1:1)

Sources & evidence

ORD record
ord-ff56d522faa54c379f2ff6866cf26c3e
Source dataset
uspto-grants-2013_12
Patent number
US08618023B2

Reaction notes

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