1-Propanol → 3,5-Difluoro-2-hydrazinylpyridine

HRID 1353113Notes

Reaction equation

HRID 1353113 reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.O.[NH2:11][NH2:12].C(O)CC>ClC>[NH:11]([C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1)[NH2:12]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 24654Hydrazine hydrate (1:1)HCID 27832872,3,5-Trifluoropyridine

Product 1

HCID 211023053,5-Difluoro-2-hydrazinylpyridineYield 85.6%

Reagents, catalysts & solvents 1

HCID 6327Methyl ChlorideSolvent

Procedure

6.65 g of the compound obtained in Step 3 and 4.6 ml of hydrazine monohydrate were added to 100 ml of n-propanol. The resulting mixture was refluxed for 6 hours, and distilled under a reduced pressure to remove the solvent. The residue thus obtained was dissolved in 80 ml of chloromethane, washed with water, and dried over anhydrous magnesium sulfate. The resulting organic layer was concentrated under a reduced pressure to obtain 6.20 g (yield: 85.6%) of the title compound.

Workup

  1. temperatureThe resulting mixture was refluxed for 6 hours
  2. distillationdistilled under a reduced pressure
  3. customto remove the solvent
  4. customThe residue thus obtained
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe resulting organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-22027eb61b6f409cbc9e494dd77a6c9f
Source dataset
uspto-grants-2007_05
Patent number
US07220863B2

Reaction notes

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