Chloroacetyl chloride → 5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

HRID 648971Notes

Reaction equation

HRID 648971 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=[O:19]>[SH-].[C+4].[SH-].[SH-].[SH-]>[Cl:1][CH2:2][C:3]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][C:11](=[O:19])[CH2:12]2)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-oneYield 35.8%

Reagents, catalysts & solvents 1

HCID 178420937HCID 178420937, compoundSolvent

Procedure

α-Chloroacetyl chloride (47.4 g) and 80.0 g of finely-ground anhydrous aluminum chloride were suspended in 100 ml of carbon bisulfide under ice-cooling. Oxindol (26.6 g) was added thereto with vigorous stirring and the mixture was refluxed for about 3 hours. Then the solvent was removed under reduced pressure, and the residue was poured into 1 l of ice-water and allowed to cool for a while. Crystals which precipitated were collected by filtration, washed successively with water, methanol, and diethyl ether, and dried to give 15 g of 5-(α-chloroacetyl)oxindol.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed for about 3 hours
  3. customThen the solvent was removed under reduced pressure
  4. additionthe residue was poured into 1 l of ice-water
  5. temperatureto cool for a while
  6. customCrystals which precipitated
  7. filtrationwere collected by filtration
  8. washwashed successively with water, methanol, and diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-5c6fce3289d14d07b74d1f39d208179a
Source dataset
uspto-grants-1988_04
Patent number
US04737501

Reaction notes

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