Ammonium formate → 4-[4-(Trifluoromethoxy)phenoxy]pyridine

HRID 1799513Notes

Reaction equation

HRID 1799513 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[F:19][C:2]([F:1])([F:18])[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68486955HCID 68486955, compound

Product 1

HCID 453809774-[4-(Trifluoromethoxy)phenoxy]pyridineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

After 4-[4-(Trifluoromethoxy)phenoxy]pyridine-N-oxide (50 mg) was dissolved in ethanol (1.8 mL) and 10 w/w % palladium on carbon (4 mg) was added. And then Ammonium formate (120 mg) was added. The resulting mixture was stirred at 20° C. for 6 hr. The reaction mixture was filtered to remove the catalyst followed by concentration in vacuo to give a residual substance. And the a residual substance was extracted with dichloromethane. The extract was condensed under reduced pressure to give 46 mg (98% yield) of a colorless oily target compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationfollowed by concentration in vacuo
  4. customto give a residual substance
  5. extractionAnd the a residual substance was extracted with dichloromethane
  6. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-8cc03881e8dc414dad07b47ddcdd2e07
Source dataset
uspto-grants-2013_01
Patent number
US08344148B2

Reaction notes

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