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

HRID 1371862Notes

Reaction equation

HRID 1371862 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. customambient 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-6117480c55154023b150b0b3a17679b8
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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