Water → HCID 178477830, compound

HRID 571429Notes

Reaction equation

HRID 571429 reaction equation
[Cl:1][O-].[Na+].[Cl:4][C:5]1[N:10]=[CH:9][C:8]2[CH:11]=[N:12][NH:13][C:7]=2[CH:6]=1.O.S([O-])([O-])=O.[Na+].[Na+]>CCO>[Cl:1][C:11]1[C:8]2[CH:9]=[N:10][C:5]([Cl:4])=[CH:6][C:7]=2[NH:13][N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 23665760Sodium HypochloriteHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridine

Product 1

HCID 178477830HCID 178477830, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hypochlorite (121 mL, 195 mmol) was gradually added to a suspension of 6-chloro-1H-pyrazolo[4,3-c]pyridine (10 g, 65.1 mmol) in EtOH (100 mL) at 0° C. The reaction mixture was then stirred at room temperature for 10 minutes. Water and sodium sulfite (24.62 g, 195 mmol) were added, forming a clear solution, and the mixture was extracted with EtOAc. The organic phase was concentrated in vacuo to give 3,6-dichloro-1H-pyrazolo[4,3-c]pyridine (11.6 g, 61.7 mmol, 95% yield). MS ESI calc'd. for C6H4Cl2N3 [M+H]+ 188, found 188.

Workup

  1. customforming a clear solution
  2. extractionthe mixture was extracted with EtOAc
  3. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-08f5282e08564626b02aaf2f47bd77a4
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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