Abstract
Dropwise addition of glacial acetic acid solution of o-toluidine and acrolein diacetate into the refluxing solution of ferric chloride and hydrochloric acid in glacial acetic acid afforded 8-methylquinoline in 30.9% yield. The same treatment of m- and p-toluidines respectively gave 7- and 6-methylquinolines, while o- and p-anisidines respectively gave 8- and 6-methoxyquinolines. Several kinds of other aromatic primary amines produced the corresponding quinoline derivatives but the yield of 6-nitroquinoline from p-nitroanlllne was very unsatisfactory, and 4-aminopyridine did not afford 1, 6-naphthyridlne. 4-Aminopyridine 1-oxide afforded 1, 6-naphthyridine 6-oxide in a low yield. In these reactions, ferric chloride acts as an oxidant and ferrous chloride precipitated out from the reaction mixture.
Phenylhydroxylamine and acrolein diacetate produced quinoline by the same procedure but there was a by-product formation of a small amount of aniline in this reaction and precipitation of ferrous chloride was not observed.
