Ethenamine, N,N-dimethyl-2-[2-nitro-6-(trifluoromethyl)phenyl]-, (1E)- → 4-(Trifluoromethyl)-1H-indole

HRID 1930847Notes

Reaction equation

HRID 1930847 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:6]=1[N+:15]([O-])=O>CO.[Pd]>[F:14][C:11]([F:12])([F:13])[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:5]=1[CH:4]=[CH:3][NH:15]2

Participants

4

Reactant 1

HCID 57753441Ethenamine, N,N-dimethyl-2-[2-nitro-6-(trifluoromethyl)phenyl]-, (1E)-

Product 1

HCID 198037034-(Trifluoromethyl)-1H-indoleYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7.7 mmol Dimethyl-[(E)-2-(2-nitro-6-trifluoromethyl-phenyl)-vinyl]-amine was dissolved in 20 ml methanol. 200 mg of palladium 5% on charcoal was added and the reaction mixture hydrogenated at room temperature and atmospheric pressure. When no further hydrogen is absorbed (ca. 3 hours), the reaction mixture is filtered, concentrated and dissolved in diethyl ether. The organic phase is washed with 2 M hydrochloric acid and brine and concentrated to yield the title compound as a yellowish solid. Yield=58%. MS (m/e): 184.9 ([M+H]+, 100%).

Workup

  1. customhydrogenated at room temperature
  2. customWhen no further hydrogen is absorbed (ca. 3 hours)
  3. filtrationthe reaction mixture is filtered
  4. concentrationconcentrated
  5. dissolutiondissolved in diethyl ether
  6. washThe organic phase is washed with 2 M hydrochloric acid and brine
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7280f9d4b4e04a8ca5fa952520bb1734
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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