2-Amino-5-methylpyridine → 6-Methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=1.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]2[N:16]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)[N:14]=2)[CH:17]=1

Participants

Procedure

59.5 g (0.2 mole) of 1-bromo-2-(4-nitrophenyl)-2-ethanone, 21.6 g (0.2 mole) of 2-amino-5-methylpyridine and 34 g of sodium bicarbonate are reacted in 200 ml of 95% strength ethanol. Stirring and refluxing are maintained for 3 hours, and the reaction mixture is then cooled and the ethanol evaporated off under reduced pressure. The evaporation residue is stirred in 700 ml of water at 70° C. for 3 hours, and the insoluble material is then filtered off, washed with 50 ml of ethanol and then ether and dried. M.p. 237°-239° C.