2-Chloroacetophenone → 2-phthalimido-acetophenone

HRID 1256237Notes

Reaction equation

HRID 1256237 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K].[OH-].[Na+]>CN(C=O)C.C(Cl)Cl>[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N:15]1[C:11](=[O:21])[C:12]2[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:14]1=[O:16]

Participants

6

Reactant 3

HCID 107572-ChloroacetophenoneHCID 14798Sodium HydroxideHCID 24194345Phthalimide potassium salt

Product 1

HCID 2430382-phthalimido-acetophenoneYield 82.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A 250 ml round-bottomed flask equipped with a magnetic stirrer is charged with 30 g of 2-chloroacetophenone and 36.3 g of potassium phthalimide in 120 ml of DMF. After 4 h at RT, the mixture is concentrated under vacuum. The solid obtained is taken up in 120 ml of DCM and 100 ml of 1 sodium hydroxide solution. The organic phase is washed with saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated under vacuum. The solid obtained is triturated in diisopropyl ether. The insolubles are filtered off and dried under vacuum to give 42.6 g of 2-(2-oxo-2-phenylethyl)-1H-isoindole-1,3(2H)-dione in the form of a beige solid, which is used as it is in the following step.

Workup

  1. customA 250 ml round-bottomed flask equipped with a magnetic stirrer
  2. concentrationthe mixture is concentrated under vacuum
  3. customThe solid obtained
  4. washThe organic phase is washed with saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe solid obtained
  9. customis triturated in diisopropyl ether
  10. filtrationThe insolubles are filtered off
  11. customdried under vacuum

Sources & evidence

ORD record
ord-4bc3d116565f4009b5804525b26c3071
Source dataset
uspto-grants-2013_06
Patent number
US08461175B2

Reaction notes

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