Ethanol → 7-Benzyloxyoxindole

HRID 1386280Notes

Reaction equation

HRID 1386280 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15](=S)[CH:14]2C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([OH:22])C>[Ni]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15](=[O:22])[CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 217172407-Benzyloxy-3-methylthiooxindole

Product 1

HCID 217172307-BenzyloxyoxindoleYield 71%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

7-Benzyloxy-3-methylthiooxindole (610 mg, 2.1 mmol), (EP 8226), was dissolved in hot ethanol (60 ml). The mixture was allowed to cool and Rainey Nickel (40 ml volume, prewashed with ethanol) was added and the mixture was stirred at ambient temperature for 1.5 hours. The insolubles were removed by filtration and the filter pad was thoroughly washed with ethanol. The solvent was removed from the filtrate by evaporation and the residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (40/60) to give 7-benzyloxyoxindole (395 mg, 71%).

Workup

  1. temperatureto cool
  2. customThe insolubles were removed by filtration
  3. washthe filter pad was thoroughly washed with ethanol
  4. customThe solvent was removed from the filtrate by evaporation
  5. customthe residue was purified by column chromatography
  6. washeluting with ethyl acetate/petroleum ether (40/60)

Sources & evidence

ORD record
ord-1ca4ad583cf34560b5afca80a185cf4d
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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