Hydrazine hydrate (1:1) → HCID 178506292, compound

HRID 1943879Notes

Reaction equation

HRID 1943879 reaction equation
O.[NH2:2][NH2:3].[F:4][C:5]([F:16])([F:15])[C:6]([C:8]1[C:9](F)=[N:10][CH:11]=[CH:12][CH:13]=1)=O>C(O)C>[F:4][C:5]([F:16])([F:15])[C:6]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:3][N:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53416101HCID 53416101, compound

Product 1

HCID 178506292HCID 178506292, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (3.06 mL, 63.0 mmol) was added to 2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethanone (1.9 g, 9.0 mmol) in absolute ethanol (50 mL), and the mixture was heated to reflux overnight. The cooled reaction mixture was evaporated to afford a solid, which was partitioned between water and ethyl acetate. The aqueous layer was extracted with another portion of ethyl acetate. The combined ethyl acetate extracts were washed twice with brine, dried over magnesium sulfate, filtered, and evaporated to yield 3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine (1.43 g, 85%) as a solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customThe cooled reaction mixture
  4. customwas evaporated
  5. customto afford a solid, which
  6. customwas partitioned between water and ethyl acetate
  7. extractionThe aqueous layer was extracted with another portion of ethyl acetate
  8. washThe combined ethyl acetate extracts were washed twice with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-9fc5a8c08215446682046fd4e4f172ba
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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