Methanol → 5-(Trifluoromethyl)oxindole

HRID 971430Notes

Reaction equation

HRID 971430 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=S)[CH:6]2C.C[OH:17]>[Ni].C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:17])[CH2:6]2

Participants

5

Reactant 2

HCID 887MethanolHCID 20289277HCID 20289277, compound

Product 1

HCID 37344575-(Trifluoromethyl)oxindole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4.0 g. of 5-trifluoromethyl-3-methylthio-oxindole, 20 g. of Raney Nickel and 100 ml. of methanol is refluxed for 4 days, cooled, treated with methylene chloride, filtered to remove the Raney Nickel and the filtrate concentrated in vacuo to obtain 5-trifluoromethyl-oxindole, m.p. 188°-190° C.

Workup

  1. additionA mixture of 4.0 g
  2. temperaturecooled
  3. filtrationfiltered
  4. customto remove the Raney Nickel
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-53874bba8b77431c8985de867ba5b9ed
Source dataset
uspto-grants-1979_07
Patent number
US04160032

Reaction notes

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