[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.Br[N:10]1[C:14](=O)CC[C:11]1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.Cl>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:10]([CH3:14])[CH3:11])[N:3]=1
To 2-chloro-6-methylpyridine (38.3 g, 0.30 mole) in 300 ml of carbon tetrachloride is added N-bromosuccinimide (67.0 g, 0.375 mole) and benzoyl peroxide (1.0 g). The mixture is stirred at reflux for 22 hours. Then it is cooled to 10° and is filtered. Into the carbon tetrachloride solution of crude 2-chloro-6-bromomethylpyridine is bubbled dimethylamine with ice bath cooling. The mixture is allowed to stand at room temperature overnight. After removal of the dimethylamine hydrobromide by filtration the carbon tetrachloride filtrate is concentrated in vacuo to a dark oil. The oil is taken up in hexane and the product is extracted into 6 N hydrochloric acid (0.30 mole). The acid extract is made alkaline with sodium hydroxide and the product is extracted into benzene. After removal of the benzene the product is distilled. The yield is 42%, b.p. 108°-110° at 3.3 mm, n25D 1.5206.
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