Hydrochloric Acid → 6-Chloro-1H-pyrazolo[4,3-c]pyridin-3-ol

HRID 588079Notes

Reaction equation

HRID 588079 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]([NH:13][NH2:14])[C:7]([C:8]([O-])=[O:9])=[CH:6][N:5]=1.Cl>C(O)C>[Cl:3][C:4]1[N:5]=[CH:6][C:7]2[C:8](=[O:9])[NH:14][NH:13][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1317344276-Chloro-4-hydrazinylnicotinate

Product 1

HCID 1182717496-Chloro-1H-pyrazolo[4,3-c]pyridin-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 50-L reactor was placed ethanol (22 L), sodium hydroxide (800 g, 20.00 mol), and 6-chloro-4-hydrazinylnicotinate (2700 g, 13.39 mol). The resulting solution was stirred for 2 h at room temperature. The pH value of the solution was adjusted to 7 with HCl. The solid was filtered out. The filtrate was concentrated in vacuo to give 6-chloro-1H-pyrazolo[4,3-c]pyridin-3(2H)-one, which was carried onto the next step without further purification. MS ESI calc'd. for C6H4ClN3O [M+1]+ 170. found 170.

Workup

  1. customInto a 50-L reactor was placed
  2. filtrationThe solid was filtered out
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ef9468aab610417483b9d512c7b18000
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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