Phenylacetyl chloride → 2-(1,3-Isoindolinedion-2-yl)-5-(2-phenylacetyl)indane

HRID 1598562Notes

Reaction equation

HRID 1598562 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1(=[O:30])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[N:12]1[CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[C:11]1(=[O:30])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[N:12]1[CH:21]1[CH2:22][C:23]2[C:28](=[CH:27][CH:26]=[C:25]([C:8](=[O:9])[CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:24]=2)[CH2:29]1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 109998862-(1,3-Isoindolinedion-2-yl)indane

Product 1

HCID 189297702-(1,3-Isoindolinedion-2-yl)-5-(2-phenylacetyl)indaneYield 72.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

0.70 g of phenylacetic acid chloride dissolved in 5 ml of dichloroethane was added under ice cooling to 1.00 g of 2-(1,3-isoindolinedion-2-yl)indane and 1.27 g of anhydrous aluminum chloride suspended in 15 ml of dichloroethane, and the mixture was stirred at the same temperature for 2 hours and then at room temperature for l hour. The reaction mixture was poured into ice water and extracted with chloroform. After the organic layer was washed with water and dried, the solvent was removed. The resulting crystals were recrystallized from ethyl acetate to obtain 1.05 g of 2-(1,3-isoindolinedion-2-yl)-5-(2-phenylacetyl)indane.

Workup

  1. waitat room temperature for l hour
  2. extractionextracted with chloroform
  3. washAfter the organic layer was washed with water
  4. customdried
  5. customthe solvent was removed
  6. customThe resulting crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d42ff8ad7c6e463299eb0f2a253288bd
Source dataset
uspto-grants-1998_04
Patent number
US05739132

Reaction notes

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