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

HRID 1727608Notes

Reaction equation

HRID 1727608 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-9bbedab85c924eff8d058230206dc72f
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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