Dichloromethane → 2-Methyl-7-dimethylaminomethyl-8-hydroxy-imidazo[1,2-a]-pyridin-3-acetonitrile
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]2[C:11]=1[CH2:12][C:13]#[N:14].[I-].C[CH:17]=[N+:18]=[CH:19]C.[CH2:21](Cl)Cl>>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([OH:10])=[C:8]([CH2:17][N:18]([CH3:19])[CH3:21])[CH:7]=[CH:6][N:5]2[C:11]=1[CH2:12][C:13]#[N:14]Participants
4
Procedure
Stir a mixture of 24 g (0.13 mol) 2-methyl-8-hydroxyimidazo[1,2-a]pyridin-3-acetonitrile and 26 g (0.14 mol) N,N-dimethylmethyleneammonium iodide in 4L methylene chloride at ambient temperature for 4 days. Isolate the resulting solid by filtration, treat with 200 ml dilute ammonium hydroxide and extract continuously with methylene chloride for 4 hr. Remove the methylene chloride under reduced pressure and obtain 20 g 2-methyl-7-dimethylaminomethyl-8-hydroxy-imidazo[1,2-a]-pyridin-3-acetonitrile.