Hydrochloric Acid → 2-(1,3-Isoindolinedion-2-yl)-5-(2-methylpropionyl)indane

HRID 1598560Notes

Reaction equation

HRID 1598560 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][CH:6]([CH3:10])[C:7](Cl)=[O:8].[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>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:7](=[O:8])[CH:6]([CH3:10])[CH3:5])[CH:24]=2)[CH2:29]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 109998862-(1,3-Isoindolinedion-2-yl)indane

Product 1

HCID 189297332-(1,3-Isoindolinedion-2-yl)-5-(2-methylpropionyl)indaneYield 73.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To 8.00 g of anhydrous aluminum chloride suspended in 100 ml of dichloroethane was added dropwise 3.20 g of 2-methylpropanoyl chloride dissolved in 50 ml of dichloroethane under ice cooling. Then, to the mixture was added 5.27 g of 2-(1,3-isoindolinedion-2-yl)indane, and the mixture was stirred for 3 hours. The reaction mixture was poured into ice water containing hydrochloric acid, the organic layer was collected by separation, washed with water and dried, and then the solvent was removed. The resulting crystals were recrystallized from ethyl acetate-n-hexane to obtain 4.92 g of 2-(1,3-isoindolinedion-2-yl )-5-(2-methylpropionyl)indane.

Workup

  1. customthe organic layer was collected by separation
  2. washwashed with water
  3. customdried
  4. customthe solvent was removed
  5. customThe resulting crystals were recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-e98663a244644d49b7c487da4ccbe87f
Source dataset
uspto-grants-1998_04
Patent number
US05739132

Reaction notes

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