Ethyl bromoacetate → HCID 19921001, compound

HRID 1647823Notes

Reaction equation

HRID 1647823 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([N:16]3[C:24](=[O:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[C:8]2=[O:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])([N:16]3[C:24](=[O:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[C:8]2=[O:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 19921052HCID 19921052, compound

Product 1

HCID 19921001HCID 19921001, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixed solution of 3.54 g of 1-phenyl-3-(1,3-dioxoisoindolin-2-yl)-2,3-dihydro-1H-indol-2-one, 8.4 g of ethyl bromoacetate, 2.76 g of potassium carbonate and 40 ml of acetone was stirred under argon atmosphere at room temperature overnight. After removing the solvent, water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed and dried, and then the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; chloroform:ethanol=40:1 (v.v)) and recrystallized from ether to obtain 2.20 g of 1-phenyl-3-(ethoxycarbonylmethyl)-3-(1,3-dioxoisoindolin-2-yl)-2,3-dihydro-1H-indol-2-one as colorless prism crystals. Melting point: 148° to 149° C., IR (Nujol) (cm-1 ): 1780, 1740, 1720, 1610, MS (DI, m/z): 440 (M+)

Workup

  1. customAfter removing the solvent, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent; chloroform:ethanol=40:1 (v.v))
  8. customrecrystallized from ether

Sources & evidence

ORD record
ord-12ee9949d9be472aa04496d55e7bd9f5
Source dataset
uspto-grants-1995_07
Patent number
US05434148

Reaction notes

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