Isatin → Oxindole

HRID 49597Notes

Reaction equation

HRID 49597 reaction equation
O.NN.[NH:4]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7](=O)[C:5]1=[O:6].N1C2C(=CC=CC=2)C(=O)C1=NN.N1(C2CCCCCCC2)CCCCCCN1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>C(N(C(C)C)C(C)C)C>[NH:4]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:7][C:5]1=[O:6]

Participants

7

Reactant 5

HCID 7054IsatinHCID 24654Hydrazine hydrate (1:1)HCID 57346892DiazabicycloundecaneHCID 66583054DiazabicyclooctaneHCID 178514334HCID 178514334, compound

Product 1

HCID 321710Oxindole

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineCatalyst

Procedure

in a polar solvent with hydrazine hydrate in the presence of a tertiary amine catalyst, characterized in that the isatin is converted to the corresponding isatin hydrazone at a temperature of from 15 to 185° C. which is directly reacted further by adding a diazabicyclooctane and/or diazabicycloundecane and/or ethyldiisopropylamine catalyst at temperatures of from 100 to 185° C. while distilling off the water of reaction formed to give the corresponding 2-oxindole of the formula which is then isolated by distilling off the solvent and crystallizing out of the reaction mixture.

Workup

  1. customis directly reacted further
  2. distillationwhile distilling off
  3. customthe water of reaction
  4. customformed

Sources & evidence

ORD record
ord-7fc2e312dfb6424ca413e85dab0de840
Source dataset
uspto-grants-2004_03
Patent number
US06706890B2

Reaction notes

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