Chloroacetaldehyde → 8-Methylimidazo(1,2-a)pyridine

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Reaction Steps

18.27 g of 2-amino-3-picoline was dissolved in 150 mL of water, 14.2 g of sodium hydrogen carbonate and 33.2 g of chloroacetaldehyde (40% aqueous solution) were added thereto, and then stirred at room temperature for 4 hours. The solution was adjusted to pH 10 with a 3N aqueous solution of sodium hydroxide, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were separated by filtration, and then the filtrate was concentrated to obtain 8-methylimidazo[1,2-a]pyridine [3-1] as a brown oily product.

Provenance & Evidence