[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[CH:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])=[CH:4][CH:3]=1.[C:17]([CH2:19][C:20](OCC)=[O:21])#[N:18].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:21])[C:19]([C:17]#[N:18])=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=[N:9]2)=[CH:4][CH:3]=1After 0.281 g of 3, 3, 3-trifluoro-2-oxopropanal 1-(4-chlorophenylhydrazone) was dissolved in 5 mL of pyridine, 0.304 g of ethyl cyanoacetate was added to the pyridine solution, which was followed by stirring for 5 hours at 110° C. After cooling to room temperature, the reaction mixture was poured into 3N-hydrochloric acid and extracted with diethyl ether. After the organic layer was washed with aqueous saturated sodium bicarbonate and concentrated, the residue was subjected to silica gel column chromatography (eluent: ethyl acetate/hexane =1/9), and furthermore recrystallized from a solvent mixture (toluene/hexane =1/3) to afford 0.234 g of 2-(4-chlorophenyl)-4-cyano-5-trifluoromethylpyridazin-3-one (The present compound 1-15). 1H-NMR (300 MHz, CDCl3)δ(ppm): 7.49(2H, d, J=8.8 Hz), 7.61 (2H, d, J=8.8 Hz), 8.19 (1H,s)
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