Hydrochloric Acid → 6-Bromo-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-5-bromopyridine (25.0 g, 144.5 mmol) in EtOH (150 mL), was added methyl 2-chloro-3-acetoacetate (18.6 mL, 144.5 mmol), and the mixture was refluxed at 80° C. for 12 h. Then the reaction mixture was allowed to cool to rt, and then were added 8N aqueous sodium hydroxide solution (60 mL, 480 mmol) and water (30 mL). The mixture was stirred at 80° C. for 12 h, allowed to cool to 0° C., and then neutralized by the addition of 6N hydrochloric acid (300 mL). The resulting precipitate was collected by filtration and sequentially washed with water, EtOH and diethyl ether to give the title compound (11.1 g, 30%) as a brown solid.

Provenance & Evidence