Water → 5-(2-Chloroethyl)Oxindole

HRID 1057429Notes

Reaction equation

HRID 1057429 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.ClCC(Cl)=O.C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[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

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 12052TriethylsilaneHCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 145813925-(2-Chloroethyl)OxindoleYield 65%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-Chloroacetyl-2-oxindole (prepared by the same procedure used for the preparation of O-53, except starting from chloroacetyl chloride) (4.18 g) in 30 mL of trifluoroacetic acid in an ice bath was treated with 4.65 g of triethylsilane and stirred at room temperature for 3 hours. The mixture was poured into 150 mL of water and the precipitate collected by vacuum filtration, washed with 50 mL of water and dried to give 2.53 g (65% yield) of 5-(2-chloroethyl)-2-oxindole as a reddish-brown solid.

Workup

  1. customused for the preparation of O-53,
  2. filtrationthe precipitate collected by vacuum filtration
  3. washwashed with 50 mL of water
  4. customdried

Sources & evidence

ORD record
ord-53e9c779070a46e9ba2ae6e318f598dc
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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