5-Nitro-2-(2,2,2-trifluoroethoxy)pyridine → 6-(2,2,2-Trifluoroethoxy)pyridin-3-amine

HRID 2092662Notes

Reaction equation

HRID 2092662 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[N:8][CH:9]=1)([O-])=O.[H][H]>CO.[Pd]>[F:15][C:12]([F:13])([F:14])[CH2:11][O:10][C:7]1[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6137185-Nitro-2-(2,2,2-trifluoroethoxy)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 5431566-(2,2,2-Trifluoroethoxy)pyridin-3-amineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine (20.5 g, obtained in example 108, step 1) was dissolved in methanol (160 mL). Palladium on activated charcoal (1.96 g, 10% Pd) was added and an atmosphere of hydrogen was introduced at RT. The mixture was stirred under hydrogen for 72 hours. The reaction mixture was filtered over dicalite speed plus (Acros Organics), washed with ethyl acetate and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a brown liquid (16.49 g, 91%). MS (m/e): 193.1 [MH+].

Workup

  1. filtrationThe reaction mixture was filtered over dicalite speed plus (Acros Organics)
  2. washwashed with ethyl acetate
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record
ord-dd6002a99ab8485c86ce701f21034f46
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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