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

HRID 74039Notes

Reaction equation

HRID 74039 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 stirring 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-6f8eeede01be4c1db2f51ae6c8b4fd4a
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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