Sodium Acetate → 4-Ethoxy-2-fluoropyridine

HRID 977058Notes

Reaction equation

HRID 977058 reaction equation
Cl[C:2]1[C:3]([F:12])=[N:4][CH:5]=[C:6](Cl)[C:7]=1[O:8][CH2:9][CH3:10].C([O-])(=O)C.[Na+].[H][H]>C(O)C.[Pd]>[CH2:9]([O:8][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([F:12])[CH:2]=1)[CH3:10]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 21464398HCID 21464398, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 214644144-Ethoxy-2-fluoropyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 60.5 g (0.31 mol) of 3,5-dichloro-4-ethoxy-2-fluoropyridine and 32.2 g (0.32 mol) of sodium acetate in 400 mL of ethanol in a 1 L stirred steel Parr bomb was added 3 g of 5 percent palladium on carbon catalyst. The reactor was charged with 500 pounds per square inch gauge (3550 kiloPascals) of hydrogen and heated with stirring to 100° C. for 4 hr. The mixture was cooled, filtered, and concentrated by evaporation. The residue was dissolved in ether and the resulting solution was dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by bulb to bulb distillation (60°-80° C. at 0.5 mm Hg (67 Pascals) to obtain 18.5 g (42 percent of theory) of the title compound as a colorless oil which solidified upon standing and melted at 35°-36° C.

Workup

  1. temperatureheated
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. dissolutionThe residue was dissolved in ether
  6. dry with materialthe resulting solution was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. distillationThe residue was purified by bulb to bulb distillation (60°-80° C. at 0.5 mm Hg (67 Pascals)

Sources & evidence

ORD record
ord-b7ad958ff15b4f639e3a4f63cb8f8f5f
Source dataset
uspto-grants-1997_03
Patent number
US05614469

Reaction notes

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