3-Methylsulfanyl-5-trifluoromethyl-1,3-dihydro-indol-2-one → 5-(Trifluoromethyl)oxindole

HRID 128824Notes

Reaction equation

HRID 128824 reaction equation
CS[CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[NH:5][C:4]1=[O:16]>CC(O)=O.[Zn]>[F:15][C:12]([F:13])([F:14])[C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:16])[CH2:3]2

Participants

4

Reactant 1

HCID 123514913-Methylsulfanyl-5-trifluoromethyl-1,3-dihydro-indol-2-one

Product 1

HCID 37344575-(Trifluoromethyl)oxindoleYield 90%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3-(methylthio)-5-(trifluoromethyl)oxindole (Gassman P. G., Cue B. W., Luh T-Y, J. Org. Chem. 1977;42:1344-1348) (10 g, 40 mmol) in AcOH (100 mL) was heated under reflux with Zn dust (13.3 g, 0.2 mol) for 1 hour. The mixture was cooled and filtered, and the precipitate was washed with AcOH. The combined filtrates were evaporated under reduced pressure, and the residue was diluted with 1M aqueous ammonia to give 5-trifluoromethyloxindole [VII: R1 =5-CF3, R3 =H] (7.22 g, 90%); mp (aqueous EtOH) 188.5°-191° C. (lit. [Hardtmann G. E., U.S. Pat. No. 4,160,032; Chem. Abstr, 1979;91:P107890w]; mp 188°-189° C.).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washthe precipitate was washed with AcOH
  4. customThe combined filtrates were evaporated under reduced pressure
  5. additionthe residue was diluted with 1M aqueous ammonia

Sources & evidence

ORD record
ord-a466cc9e1e6d44b283c7b6fa96093cea
Source dataset
uspto-grants-1995_11
Patent number
US05464861

Reaction notes

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