[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9](=[N:11][OH:12])[CH3:10])[CH:3]=1.[H-].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:18]=1[CH2:19]Br>CN(C)C=O>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:18]=1[CH2:19][O:12][N:11]=[C:9]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)[CH3:10]On the other hand, 0.50 g (3.05 mmol) of 1-(4,6-dimethyl-2-pyridinyl)ethanone oxime was dissolved in 10 ml of N,N-dimethylformamide, and the resultant solution was added with 0.12 g (3.00 mmol) of sodium hydride (60%, oiliness) under cooling with ice. The solution was then stirred for 30 min. at a temperature below 0° C. and then added with the whole amount of the crude product of 2-methoxy-6-methylbenzyl bromide prepared previously under cooling with ice. The resultant solution was stirred for an hour at a room temperature to complete a reaction, and the reacted solution was poured into ice water and subjected to an extraction with diethyl ether. The resultant nonaqueous layer was separated, and the separated layer was washed with water and then dried with anhydrous magnesium sulfate. The dried nonaqueous layer was then condensed under reduced pressure to produce a crude product. The crude product was then purified by means of silica gel column chromatography (eluate; hexane:ethyl acetate=7:3 (v/v)) and recrystallized in hexane to obtain the target compound in an amount of 0.30 g.
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