Sodium Cyanide → ethyl 5-cyano-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate

HRID 1249434Notes

Reaction equation

HRID 1249434 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[C-:18]#[N:19].[Na+]>CN(C=O)C>[C:18]([C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:19]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 13654084Ethyl 5-chloro-1-(pyridin-2-YL)-1H-pyrazole-4-carboxylate

Product 1

HCID 13654086ethyl 5-cyano-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylateYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7.36 g of 5-chloro-1-(2-pyridinyl)-1H-pyrazole-4-carboxylic acid, ethyl ester, 3.2 g of sodium cyanide and 25 ml of DMF was heated at approximately 100° C. for 3 hours. The reaction mixture was cooled and poured into 300 ml of ice water. The precipitated solid was collected by filtration to afford 5.79 of solid. This material was recrystallized from ethanol to provide 4.72 g of 5-cyano-1-(2-pyridinyl)-1H-pyrazole-4-carboxylic acid, ethyl ester. mp=112°-114° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe precipitated solid was collected by filtration
  3. customto afford 5.79 of solid
  4. customThis material was recrystallized from ethanol

Sources & evidence

ORD record
ord-8f906f500fe34e4e9d048b9bc49fb0f9
Source dataset
uspto-grants-1986_12
Patent number
US04631343

Reaction notes

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