Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=O.[C-:18]#[N:19].[Na+].C[N:22]([CH:24]=O)C.CN>O>[C:18]([C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:13]([NH:22][CH3:24])=[O:15])#[N:19]A 100 ml 3-neck round bottom flask was charged with 12.0 g (0.048 mol) of 99.1% pure 5-chloro-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester, 4.7 g (0.096 mol) of sodium cyanide and 28.8 ml of DMF. The resulting mixture was heated at approximately 100° C. for 6 hours and then stirred at room temperature overnight. Thirteen grams (0.17 mol) of 40% aqueous methylamine were added to the reaction mixture dropwise. The reaction mixture was stirred at room temperature for 61/2 hours and 28.8 ml of water was added. The mixture was stirred for 30 minutes and the precipitated solid was collected by filtration. The resulting solid was washed with water and vacuum dried to afford 9.2 g of 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide. The corrected yield was 73.4% and purity of the final product by high pressure liquid chromatography was 85.8%.
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