1,3-Dichloroacetone → 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine

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Reaction Steps

3.81 g of 1,3-dichloroacetone and 3.24 g of 2-amino-3-methylpyridine were dissolved in 30 ml of ethanol, and the solution was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. To the residue, 50 ml of aqueous saturated sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then recrystallized from hexane-methyl-t-butyl ether to obtain 1.52 g of 2-(chloromethyl)-8-methylimidazo[1,2-a]pyridine.

Provenance & Evidence