Water → 5-(2-Chloroethyl)Oxindole

HRID 1952912Notes

Reaction equation

HRID 1952912 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.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

5

Reactant 3

HCID 962WaterHCID 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 (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. filtrationthe precipitate collected by vacuum filtration
  2. washwashed with 50 mL of water
  3. customdried

Sources & evidence

ORD record
ord-1eea3d563e56410abc62f2ade53d495f
Source dataset
uspto-grants-2000_09
Patent number
US06114371

Reaction notes

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