75748-33-3Relevant articles and documents
Mechanism of the formation of quinoline from N-methylacetanilide studied using 13C-labeled substrates
Leete, Edward
, p. 1806 - 1809 (2007/10/02)
Pictet discovered 90 years ago that quinoline and p-toluidine were formed on heating N-methylacetanilide with zinc chloride.It has now been shown that 6-methylquinoline is also produced in this reaction.It was established by means of 13C nmr that -N-methylacetanilide affords quinoline and its 6-methyl derivative enriched at C-4. -N-Methylacetanilide yielded quinoline and -6-methylquinoline.N-Methylpropionanilide afforded 3-methylquinoline.These results are in accord with a new mechanism for the formation of quinoline, different from the one previously proposed.