Hydrazine → HCID 178507265, compound

HRID 1943909Notes

Reaction equation

HRID 1943909 reaction equation
[F:1][C:2]1([F:10])[CH2:4][CH:3]1[C:5](=O)[CH2:6][C:7]#[N:8].[NH2:11][NH2:12]>C(O)C>[F:1][C:2]1([F:10])[CH2:4][CH:3]1[C:5]1[CH:6]=[C:7]([NH2:8])[NH:12][N:11]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 670888553-(2,2-Difluorocyclopropyl)-3-oxopropanenitrile

Product 1

HCID 178507265HCID 178507265, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude 3-(2,2-difluorocyclopropyl)-3-oxo-propionitrile (2 g) was dissolved in ethanol (18 mL) and treated with hydrazine (2.5 mL, 0.050 mol) at reflux for 24 hours. The reaction mixture was concentrated, diluted with brine and extracted into ethyl acetate (2×50 mL). The combined organic layers were dried (MgSO4), concentrated and purified by silica gel chromatography eluting with 1-15% methanol in methylene chloride to afford 3-(2,2-difluorocyclopropyl)-1H-pyrazol-5-amine (1.8 g, 54% yield).

Workup

  1. temperatureat reflux for 24 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with brine
  4. extractionextracted into ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography
  8. washeluting with 1-15% methanol in methylene chloride

Sources & evidence

ORD record
ord-13bd41577a4d4e259942b8acba0ce5dc
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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