5-Methoxy-2-nitro-4-(trifluoromethyl)benzene acetonitrile → 5-Methoxy-6-(trifluoromethyl)-1H-indole

HRID 427728Notes

Reaction equation

HRID 427728 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:15]([F:18])([F:17])[F:16])=[CH:5][C:6]([N+:12]([O-])=O)=[C:7]([CH2:9][C:10]#N)[CH:8]=1>C(O)C.O.C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[C:15]([F:18])([F:17])[F:16])[NH:12][CH:10]=[CH:9]2

Participants

5

Reactant 1

HCID 107777195-Methoxy-2-nitro-4-(trifluoromethyl)benzene acetonitrile

Product 1

HCID 108225525-Methoxy-6-(trifluoromethyl)-1H-indoleYield 96.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 19096565Water ethanolSolvent

Procedure

(5-Methoxy-2-nitro4-trifluoromethylphenyl)acetonitrile (D7) (85 g, 0.327 mol) in ethanol/water (9:1, 1.6 l) and glacial acetic acid (16 ml) was hydrogenated over 10% palladium on carbon (50 g) at 50 psi for 0.5 h at room temperature. The reaction mixture was filtered and evaporated in vacuo. The residue was partitioned between aqueous K2CO3 (1 l) and dichloromethane (2×1 l) and the combined organic extract was dried (Na2SO4) and evaporated to afford the title indole (67.63 g, 96%) as a grey solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. customThe residue was partitioned between aqueous K2CO3 (1 l) and dichloromethane (2×1 l)
  4. extractionthe combined organic extract
  5. dry with materialwas dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-794559456b234bb29e5aabc7b9490c1b
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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