Nitric Acid → 6-Bromo-3-nitroimidazo[1,2-a]pyridine

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Reaction Steps

A solution of 24 gms. (.122 mole) of 6-bromoimidazo [1,2-a] pyridine in 80 ml. of concentrated sulfuric acid is treated dropwise with 24 ml. of concentrated nitric acid while maintaining a temperature of 15° C with external cooling. When the addition is complete, the reaction mixture is stirred at room temperature for 1/2 hour and poured onto 450 gm. of ice. The pH of the mixture is adjusted to pH 4 with aqueous potassium hydroxide and the resultant solids are collected by filtration. The filter cake is washed with water and dried. Recrystallization from methylene chloride-hexane yields pure 3-nitro 6-bromoimidazo [1,2-a] pyridine m.p. 160°-161° C.

Provenance & Evidence