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

HRID 2404764Notes

Reaction equation

HRID 2404764 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-d84020f975614a36bde6970a7381df59
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

Loading…