[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[O:12])[CH2:8][C:9](=[O:11])[CH3:10].[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]([O:22]CC)=O)[CH:15]=1.[H-].[Na+]>O1CCCC1>[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20](=[O:22])[CH2:10][C:9](=[O:11])[CH2:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:12])[CH:15]=1A mixture of 21.3 g (131 mmol) of 1-pyridin-2-ylbutane-1,3-dione and 36.3 g (196 mmol) of ethyl 4-chloropyridine-2-carboxylate in 100 ml of absolute tetrahydrofuran is added dropwise to 10.43 g (261 mmol, about 60% dispersion) of sodium hydride in 200 ml of absolute tetrahydrofuran at the boiling point over the course of two hours. The mixture is stirred for another two hours at 70° C., evaporated on a rotary evaporator, and 200 ml of water are subsequently added cautiously at 4° C. The mixture is rendered neutral with 5N hydrochloric acid, and 1-(4-chloropyridin-2-yl)-5-pyridin-2-ylpentane-1,3,5-trione is filtered off as a yellowish green solid The dried, sparingly soluble product is processed further without any particular purification steps.
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