(2-Nitro-5-trifluoromethylphenyl) acetonitrile → 5-(trifluoromethyl)-1H-indole

HRID 427725Notes

Reaction equation

HRID 427725 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[CH2:14][C:15]#[N:16])([O-])=O>CCO.O.C(O)(=O)C.[Pd]>[F:13][C:10]([F:11])([F:12])[C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[NH:16][CH:15]=[CH:14]2

Participants

5

Reactant 1

HCID 18357729(2-Nitro-5-trifluoromethylphenyl) acetonitrile

Product 1

HCID 27630755-(trifluoromethyl)-1H-indoleYield 65%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 19096565Water ethanolSolvent

Procedure

(2-Nitro-5-trifluoromethylphenyl)acetonitrile (D4, 1.9 g, 0.0088 mole) in 90% EtOH/H2O (25 ml) and glacial acetic acid (0.25 ml) was hydrogenated at 50 psi in the presence of 10% Pd/C (1 g) at room temperature for 2 hours. After filtration of the catalyst through kieselguhr, the solvent was removed in vacuo. The residue was basified with saturated aqueous potassium carbonate solution, extracted into DCM, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 30% ethyl acetate/60-80° petroleum ether to afford the title compound (1.0 g, 65%) as an off white solid.

Workup

  1. filtrationAfter filtration of the catalyst through kieselguhr
  2. customthe solvent was removed in vacuo
  3. extractionextracted into DCM
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with 30% ethyl acetate/60-80° petroleum ether

Sources & evidence

ORD record
ord-5a2a7a79817943c9824aa79bfd3dfec3
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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