4-(Trifluoromethyl)aniline → 5-(Trifluoromethyl)oxindole

HRID 414264Notes

Reaction equation

HRID 414264 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.Cl[O:13][C:14](C)(C)[CH3:15].CSCC(OCC)=O>[Ni].C(N(CC)CC)C>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[C:8]2[C:6](=[CH:5][CH:4]=1)[NH:7][C:14](=[O:13])[CH2:15]2

Participants

6

Reactant 3

HCID 99644-(Trifluoromethyl)anilineHCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 37344575-(Trifluoromethyl)oxindole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8471TriethylamineSolvent

Procedure

In analogous fashion, 4-trifluoromethylaniline was reacted with t-butyl hypochlorite, ethyl 2-(methylthio)acetate and triethylamine followed by reduction of the 3-thiomethyl-5-trifluoromethyl-2-oxindole thus obtained with Raney nickel, to give 5-trifluoromethyl-2-oxindole, m.p. 189.5°-190.5° C.

Sources & evidence

ORD record
ord-69a9ab89be9f4651bd0cf5bf0bbabf7f
Source dataset
uspto-grants-1988_12
Patent number
US04791131

Reaction notes

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