Sodium Cyanide → Ethyl 1-(4-bromophenyl)-5-cyano-1H-pyrazole-4-carboxylate

HRID 280454Notes

Reaction equation

HRID 280454 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C-:19]#[N:20].[Na+]>CN(C=O)C>[C:19]([C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:20]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 53302192Ethyl 1-(4-bromophenyl)-5-chloro-1H-pyrazole-4-carboxylate

Product 1

HCID 13654089Ethyl 1-(4-bromophenyl)-5-cyano-1H-pyrazole-4-carboxylateYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.6 g of 5-chloro-1-(4-bromophenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester in 30 ml of DMF with 2 g of sodium cyanide was heated at approximately 95° C. for 3 hours. The reaction mixture was poured into ice water and the precipitated solid was collected by filtration. The product was recrystallized from 3 A alcohol to afford 5.3 g of 5-cyano-1-(4-bromophenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester. MP=104°-105° C.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customThe product was recrystallized from 3 A alcohol

Sources & evidence

ORD record
ord-b2283f4ae94b4b11b38246ed994e2dcc
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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