Potassium Cyanide → 5-Cyanoethyl-2-oxindole

HRID 1952944Notes

Reaction equation

HRID 1952944 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 dimethyl-sulfoxide and heated to 90° C. 5-Chloroethyl-2-oxindole (3.0 g) dissolved in 5 mL 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, dried and then chromatographed on silica gel (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. customchromatographed on silica gel (5% methanol in chloroform)

Sources & evidence

ORD record
ord-ffa641fc834540c4af85fe88eaa11cd5
Source dataset
uspto-grants-2000_09
Patent number
US06114371

Reaction notes

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