Ethylene Glycol → 3-(2-Hydroxyethyl)indolin-2-one

HRID 1529738Notes

Reaction equation

HRID 1529738 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH2:11](O)[CH2:12][OH:13]>[Ni]>[OH:13][CH2:12][CH2:11][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 321710Oxindole

Product 1

HCID 108992203-(2-Hydroxyethyl)indolin-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A stifling mixture of oxindole (5.7 g, 43 mmol) and Raney nickel (10 g) in ethane-1,2-diol (100 mL) was heated in an autoclave. After the reaction was complete, the mixture was filtered and the excess of diol was removed under vacuum. The residual oil was triturated with hexane to give 3-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one as a colorless crystalline solid (4.6 g, 70%).

Workup

  1. temperaturewas heated in an autoclave
  2. filtrationthe mixture was filtered
  3. customthe excess of diol was removed under vacuum
  4. customThe residual oil was triturated with hexane

Sources & evidence

ORD record
ord-f7390bc4c484417da89eadbe2f6e5eaa
Source dataset
uspto-grants-2015_07
Patent number
US09090619B2

Reaction notes

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