Dimethyl Sulfoxide → 5-(2-Carboxyethyl)-2-oxindole

HRID 413725Notes

Reaction equation

HRID 413725 reaction equation
[C-]#N.[K+].C(CCC1C=C2C(=CC=1)N[C:12](=[O:17])C2)#N.Cl[CH2:19][CH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:30])[CH2:24]2.CS(C)=[O:33]>>[C:12]([CH2:19][CH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:30])[CH2:24]2)([OH:17])=[O:33]

Participants

4

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 145813925-(2-Chloroethyl)OxindoleHCID 865845215-Cyanoethyl-2-oxindole Potassium cyanide

Product 1

HCID 219257025-(2-Carboxyethyl)-2-oxindoleYield 42%

Conditions

Temperature
90 °C

Procedure

Synthesis of 5-Cyanoethyl-2-indolinone Potassium cyanide (2.02 g) was added to 15 mL of dimethylsulfoxide and heated to 90° C. 5-Chloroethyl-2-indolinone (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-94216d7faaf749b6bda23cf837f068cf
Source dataset
uspto-grants-2003_05
Patent number
US06569868B2

Reaction notes

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