Cl[C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[CH:6][CH:5]=[C:4]([CH2:17][CH3:18])[N:3]=1.[CH2:19]([NH2:21])[CH3:20].Cl.[OH-].[Na+]>>[Cl:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[C:8]([C:7]1[C:2]([NH:21][CH2:19][CH3:20])=[N:3][C:4]([CH2:17][CH3:18])=[CH:5][CH:6]=1)=[O:16]A mixture of 2-chloro-3-(3-chlorobenzoyl)-6-ethylpyridine (3.4 g, 12 mmol) and 70% ethylamine aqueous solution (15 ml) was sealed in a tube and stirred at 100° C. for 4 hours. The reaction solution was cooled to room temperature and then transferred into a separating funnel. This was acidified by adding 1 N hydrochloric acid, vigorously shaken and then alkalified by adding 1 N sodium hydroxide aqueous solution. This was extracted with chloroform, the resulting organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and then the filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3-(3-chlorobenzoyl)-6-ethyl-2-ethylaminopyridine (2.6 g, 76%) as a yellow oily material.
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