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

HRID 401371Notes

Reaction equation

HRID 401371 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-923023eac3304e00814ee021f7b24ab6
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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