Methanol → 2,5-Difluoropyridin-4-amine

HRID 610235Notes

Reaction equation

HRID 610235 reaction equation
CO.[NH2:3][C:4]1[C:9](Cl)=[C:8]([F:11])[N:7]=[C:6](Cl)[C:5]=1[F:13]>[C].[Pd].C(N(CC)CC)C>[NH2:3][C:4]1[C:5]([F:13])=[CH:6][N:7]=[C:8]([F:11])[CH:9]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 221211852,5-Dichloro-3,6-difluoropyridin-4-amine

Product 1

HCID 221211752,5-Difluoropyridin-4-amineYield 90.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To 40 ml of methanol were added 4.5 g of 4-amino-2,5-dichloro-3,6-difluoropyridine and 4.5 g of triethylamine together with 0.40 g of 10% palladium carbon, and the mixture was hydrogenated at 50° C. for 12 days. The catalyst was separated by filtration, and the solvent and the like were distilled off under reduced pressure. To the residue was added 100 ml of chloroform, and the mixture was washed with 10 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue were added 1.5 g of triethylamine, 0.35 g of 10% palladium on carbon, and 30 ml of methanol, and the mixture was hydrogenated at 50° C. for 41 hours. The catalyst was separated by filtration, and the solvent and the like were distilled off under reduced pressure. To the residue was added 100 ml of chloroform, and the mixture was washed with 10 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 2.67 g of the title compound as precipitate as a colorless solid.

Workup

  1. customThe catalyst was separated by filtration
  2. distillationthe solvent and the like were distilled off under reduced pressure
  3. additionTo the residue was added 100 ml of chloroform
  4. washthe mixture was washed with 10 ml of distilled water
  5. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue were added 1.5 g of triethylamine, 0.35 g of 10% palladium on carbon, and 30 ml of methanol
  8. waitthe mixture was hydrogenated at 50° C. for 41 hours
  9. customThe catalyst was separated by filtration
  10. distillationthe solvent and the like were distilled off under reduced pressure
  11. additionTo the residue was added 100 ml of chloroform
  12. washthe mixture was washed with 10 ml of distilled water
  13. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21b56d2f74154aacb19c3f78ca1b270f
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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