[C-:1]#[N:2].[Na+].Cl[C:5]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]=[CH:7][C:6]=1[C:16]([O:18]CC)=O.[CH3:21][NH2:22].O>CN(C=O)C>[C:1]([C:5]1[N:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:8]=[CH:7][C:6]=1[C:16]([NH:22][CH3:21])=[O:18])#[N:2]
Four and seven tenths grams (0.096 mol) of sodium cyanide were added to a solution of 12.0 g (0.048 mol) of 94.66% pure 5-chloro-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester in 28.8 ml of DMF at room temperature. The solution was heated for 6 hours at 100° C. and cooled to room temperature. The reaction mixture was stirred overnight and 13.0 g (0.17 mol) of 40% aqueous methylamine was added dropwise. The resulting mixture was stirred for 6 hours at room temperature and 28.8 ml of water was slowly added. The mixture was stirred for 10 minutes and the precipitated solid was collected by filtration. This solid was washed with water and vacuum dried to provide 8.3 g of 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide as a white solid. The product analyzed 95.81% pure by high pressure liquid chromatography, corresponding to a corrected yield of 77.4% product.
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