Trifluoroacetic acid → 5-(2-Chloroethyl)Oxindole

HRID 1857554Notes

Reaction equation

HRID 1857554 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>CCCCCC>[Cl:1][CH2:2][CH2:3][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 145813925-(2-Chloroethyl)OxindoleYield 91%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

5-Chloroacetyl-2-oxindole (7.0 g) was added to 25 mL of trifluoroacetic acid and the mixture cooled in an ice bath with stirring. Triethylsilane (12.3 mL) was added dropwise over 2 minutes. The reaction was then stirred at room temperature for 4 hours and poured into ice water. Hexane was added, the mixture stirred vigorously, and the solid collected by vacuum siltation and washed with hexane to give 5.9 g (91% yield) of the product as a white solid.

Workup

  1. temperaturethe mixture cooled in an ice bath
  2. stirringThe reaction was then stirred at room temperature for 4 hours
  3. stirringthe mixture stirred vigorously
  4. customthe solid collected by vacuum siltation
  5. washwashed with hexane

Sources & evidence

ORD record
ord-f07b0d32fafc4b4bb5ac25c5e5a005b4
Source dataset
uspto-grants-2000_11
Patent number
US06147106

Reaction notes

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