HCID 73740491, compound → 6-(Trifluoromethoxy)-1H-indole

HRID 1666803Notes

Reaction equation

HRID 1666803 reaction equation
CN([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][C:7]=1[N+:17]([O-])=O)C>C(O)C.[Ni]>[F:16][C:13]([F:14])([F:15])[O:12][C:9]1[CH:8]=[C:7]2[C:6]([CH:5]=[CH:4][NH:17]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 73740491HCID 73740491, compound

Product 1

HCID 220489586-(Trifluoromethoxy)-1H-indole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Combine N,N-dimethyl-2-(2-nitro-4-trifluoromethoxyphenyl)vinylamine (4.64 g, 16.8 mmol) and Raney® nickel (900 mg) in ethanol (100 ml). Hydrogenate at 60 psi (410 kPa) and ambient temperature. After 18 hours, filter through celite, concentrate the filtrate to residue, and chromatograph on silica gel eluting with hexanes/ethyl acetate (30/70) to give, after evaporation, the title compound as an off-white powder: mp 59° C. MS (ACPI): m/e 200.0 (M−1).

Workup

  1. customat 60 psi (410 kPa) and ambient temperature
  2. filtrationfilter through celite
  3. concentrationconcentrate the filtrate to residue, and chromatograph on silica gel eluting with hexanes/ethyl acetate (30/70)
  4. customto give
  5. customafter evaporation

Sources & evidence

ORD record
ord-9d0ef04dda02474cab3d60b48b37fd6c
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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