Sodium Hydroxide → HCID 22723421, compound

HRID 1581749Notes

Reaction equation

HRID 1581749 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[C:8]=12)([O-])=O.[Sn](Cl)(Cl)(Cl)[Cl:17].[OH-].[Na+]>Cl>[ClH:17].[ClH:17].[NH2:1][C:4]1[CH:5]=[N:6][N:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[C:8]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 21828339HCID 21828339, compound

Product 1

HCID 22723421HCID 22723421, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

0.7 g of 3,4-dinitropyrazolo[1,5-a]pyridine was added to a suspension of 11.1 g of tin chloride in 80 ml of concentrated hydrochloric acid. The reaction was monitored by thin layer chromatography (TLC). The pH of the reaction mixture was adjusted to 12 using sodium hydroxide. The aqueous phase was extracted with ethyl acetate and the organic phase was dried over sodium sulfate. The organic phase was acidified with 3 ml of hydrochloric ethanol (2.5 N HCl). The precipitate was filtered off. This gave 0.55 g of pyrazolo[1,5-a]pyridine-3,4-diamine hydrochloride, whose 1H NMR analysis (DMSO-d6, 400 MHz) (δ ppm) was as follows:

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-e8f389565fa647fc8cb70b8bf8bf3521
Source dataset
uspto-grants-2004_05
Patent number
US06730789B1

Reaction notes

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