Hydrochloric Acid → 2-Amino-3,5-difluoro-6-(methylamino)pyridine

HRID 610181Notes

Reaction equation

HRID 610181 reaction equation
Cl.[CH2:2]([NH:9][C:10]1[C:15]([F:16])=[CH:14][C:13]([F:17])=[C:12]([NH:18]C)[N:11]=1)C1C=CC=CC=1>[Pd].CO>[NH2:18][C:12]1[C:13]([F:17])=[CH:14][C:15]([F:16])=[C:10]([NH:9][CH3:2])[N:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 221212002-Benzylamino-3,5-difluoro-6-(methylamino)pyridine

Product 1

HCID 158962962-Amino-3,5-difluoro-6-(methylamino)pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixed solution of 10 ml of methanol and 1 ml of concentrated hydrochloric acid were added all amount of the above described 2-benzylamino-3,5-difluoro-6-(methylamino)pyridine together with 0.55 g of 10% palladium on carbon, and the mixture was hydrogenated at 50° C. overnight. The catalyst was separated by filtration, and the solvent and the like were distilled off under reduced pressure. To the residue was added 50 ml of chloroform, and the mixture was washed with 50 ml of 5% aqueous solution of sodium carbonate. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The solid precipitate was collected by filtration to obtain 840 mg of the title compound as a pale gray 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 50 ml of chloroform
  4. washthe mixture was washed with 50 ml of 5% aqueous solution of sodium carbonate
  5. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-a466bff44e7447f89d9a09d4eed3be2e
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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