Hydrazine hydrate (1:1) → HCID 118271762, compound
Reaction equation
Cl[C:2]1[C:7]([C:8](OC)=[O:9])=[CH:6][N:5]=[C:4]([Cl:12])[C:3]=1[F:13].O.[NH2:15][NH2:16]>C(O)C>[Cl:12][C:4]1[N:5]=[CH:6][C:7]2[C:8](=[O:9])[NH:15][NH:16][C:2]=2[C:3]=1[F:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Methyl 4,6-dichloro-5-fluoronicotinate (5.0 g, 22.32 mmol) and hydrazine monohydrate (1.7 mL, 22.32 mmol) were dissolved in ethanol (5 mL) and stirred at 80° C. for 1 h. The reaction mixture was filtered, dissolved in MeOH, and HCl (1 N, 0.5 mL) was added. The reaction was stirred at room temperature for 4 h. The reaction mixture was then filtered and washed with water to give 6-chloro-7-fluoro-1H-pyrazolo[4,3-c]pyridin-3(2H)-one, which was carried onto the next step without further purification. MS ESI calc'd. for C6H13ClFN3O [M+1]+ 188. found 188.
Workup
- filtrationThe reaction mixture was filtered
- dissolutiondissolved in MeOH
- additionHCl (1 N, 0.5 mL) was added
- stirringThe reaction was stirred at room temperature for 4 h
- filtrationThe reaction mixture was then filtered
- washwashed with water
Sources & evidence
- ORD record
- ord-d65f289f85a241b69ba040009cac64cb
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09226922B2
Reaction notes
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