94093-78-4Relevant academic research and scientific papers
Aminomethylation of picolines
Moehrle,Pycior,Lessel
, p. 569 - 575 (2007/10/03)
Under various conditions aminomethylation of 2-methylpyridine proceeds in amounts to be isolated only with paraformaldehyde/secondary amine-hydrochloride or better using iminium salts. 4-Methylpyridine is - in contrary to literature - also aminomethylated at the methyl group giving mono- and disubstituted products. 3-Methylpyridine does not react even under drastic conditions. The benzylpyridines show a higher reactivity but a similar behaviour. 4-Benzylpyridine yields the monoalkylated product as hydrochloride or a mixture of the dihydrochloride and the quaternary derivative. The reaction mechanism explained with enamine intermediates is substantiated by MNDO calculations.
