Potassium Cyanide → 5-Cyanoethyl-2-oxindole

HRID 24435Notes

Reaction equation

HRID 24435 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 dimethylsulfoxide was added slowly with stirring, and the reaction was heated to 150° C. and stirred for 2 hours. The mixture was cooled, poured into ice water and the precipitate which formed was collected by vacuum filtration, washed with water, and dried to give crude product. The crude material was chromatographed on silica gel (5% methanol in chloroform) to give 1.2 g (42%) of 5-cyanoethyl-2-oxindole.

Workup

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

Sources & evidence

ORD record
ord-f98c0643a73c4a08867dc8dbbfa36a25
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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