Hydrazine → 3-(pyridin-4-yl)-1H-pyrazol-5-amine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe mixture refluxed for 3 hours
- concentrationconcentrated to dryness
- customThe residue was purified by chromatography
- 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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