Potassium Cyanide → 5-Cyanoethyl-2-oxindole

HRID 1057463Notes

Reaction equation

HRID 1057463 reaction equation
[C-:1]#[N:2].[K+].Cl[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10]2>CS(C)=O>[C:1]([CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10]2)#[N:2]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 145813925-(2-Chloroethyl)Oxindole

Product 1

HCID 101764305-Cyanoethyl-2-oxindoleYield 42%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
90 °C

Procedure

Potassium cyanide (2.0 g) was added to 15 mL of dimethylsulfoxide and heated to 90° C. 5-Chloroethyl-2-oxindole (3.0 g) dissolved in 5 mL of dimethyl sulfoxide was added slowly with stirring, and the reaction heated to 150° C. for 2 hours. The mixture was cooled, poured into ice water and the precipitate collected by vacuum filtration, washed with water, and dried to give crude product. The crude material was chromatographed on silica gel in 5% methanol in chloroform to give 1.2 g (42% yield) of the title compound.

Workup

  1. additionwas added slowly
  2. temperaturethe reaction heated to 150° C. for 2 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe precipitate collected by vacuum filtration
  5. washwashed with water
  6. customdried
  7. customto give crude product
  8. customThe crude material was chromatographed on silica gel in 5% methanol in chloroform

Sources & evidence

ORD record
ord-7c070e91fd0643cb89eb73ce9cdfbce6
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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