Water → 5-(2-Chloroethyl)Oxindole

HRID 1860779Notes

Reaction equation

HRID 1860779 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

A solution of 5-chloroacetyl-2-oxindole (4.18 g) in trifluoroacetic acid (30 ml) was cooled in an ice bath and 4.65 g of triethylsilane added. The mixture was then stirred at room temperature for 3 hours. The mixture was poured into 150 ml of water and the precipitate which formed was 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. customthe precipitate which formed
  2. filtrationwas collected by vacuum filtration
  3. washwashed with 50 ml of water
  4. customdried

Sources & evidence

ORD record
ord-40414e2690474a68b9669c147d0e7239
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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