Trifluoroacetic acid → 5-Ethyl-1,3-dihydro-2H-indol-2-one

HRID 24384

Reaction equation

HRID 24384 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)(=O)[CH3:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)[CH3:2]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052Triethylsilane2×HCID 102196435-acetyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 101541895-Ethyl-1,3-dihydro-2H-indol-2-oneYield 71%

Procedure

5-Acetyl-2-oxindole (2 g) and 15 ml of trifluoroacetic acid in an ice bath was slowly treated with 1.8 g of triethylsilane and then stirred at room temperature for 5 hours. One ml of triethylsilane was added and stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of 5-ethyl-2-oxindole as a yellow solid.

Workup

  1. stirringstirring continued overnight
  2. filtrationthe resulting precipitate collected by vacuum filtration
  3. washwashed copiously with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c8e3e385743e4295901d90ded8b42ade
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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