Hydrazine → HCID 178507285, compound

HRID 1943905Notes

Reaction equation

HRID 1943905 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=O)[CH2:8][C:9]#[N:10].[NH2:12][NH2:13]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([NH2:10])[NH:13][N:12]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 115718233-Oxo-3-(pyridin-2-yl)propanenitrile

Product 1

HCID 178507285HCID 178507285, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-Pyridyl)-3-oxopropanenitrile (3.0 g, 0.37 mol) was dissolved in ethanol (22 mL) and treated with hydrazine (1.9 mL, 0.062 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 2-20% methanol in methylene chloride to afford 3-(pyridin-2-yl)-1H-pyrazol-5-amine (3.0 g, 91% 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 2-20% methanol in methylene chloride

Sources & evidence

ORD record
ord-a1636b72dbbb4e759fb21ee6267195f9
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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