Hydrazine → HCID 178507265, compound
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux for 24 hours
- concentrationThe reaction mixture was concentrated
- additiondiluted with brine
- extractionextracted into ethyl acetate (2×50 mL)
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated
- custompurified by silica gel chromatography
- 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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