Hydrazine hydrate (1:1) → 4-chloro-1H-pyrazolo[4,3-c]pyridine
Reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>COCCOC>[Cl:1][C:2]1[C:7]2[CH:8]=[N:12][NH:13][C:6]=2[CH:5]=[CH:4][N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of 2,4-dichloropyridine-3-carbaldehyde (7.0 g) in DME (70 mL) was added hydrazine monohydrate (8.0 g) at room temperature. The reaction mixture was stirred overnight at 75° C., and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (4.0 g).
Workup
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)
Sources & evidence
- ORD record
- ord-7f68ff6a687a4beabe077440bd05a565
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371320B2
Reaction notes
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