Hydrazine → 3-(pyridin-4-yl)-1H-pyrazol-5-amine

HRID 1726402Notes

Reaction equation

HRID 1726402 reaction equation
O=[C:2]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].[NH2:12][NH2:13]>C(O)C>[N:9]1[CH:10]=[CH:11][C:6]([C:2]2[NH:13][N:12]=[C:4]([NH2:5])[CH:3]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 157315353-Oxo-3-(pyridin-4-yl)propanenitrile

Product 1

HCID 187693853-(pyridin-4-yl)-1H-pyrazol-5-amineYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3-oxo-3-(pyridin-4-yl)propanenitrile (3.40 g; Example 7, Step 1) suspended in 230 mL ethanol was added 2.92 mL hydrazine. The mixture refluxed for 3 hours and concentrated to dryness. The residue was purified by chromatography, eluting with a mixture of 10% methanol in dichloromethane to yield 0.80 g (21% yield) product as a light yellow solid. MS showed a M+1 molecular ion of m/z 161.3 by positive APCI.

Workup

  1. temperatureThe mixture refluxed for 3 hours
  2. concentrationconcentrated to dryness
  3. customThe residue was purified by chromatography
  4. washeluting with a mixture of 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-654d980b821e4caab811c155c0bd96e7
Source dataset
uspto-grants-2009_02
Patent number
US07491829B2

Reaction notes

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