Isolation and structure elucidation of the by‐product formed in the aminomethylation of α‐methylstyrene

Pál Sohár, János Lázár, Gábor Bernáth

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Aminomethylation of α‐methylstyrene (1) leads to 1,2,3,6‐tetrahydro‐4‐phenylpyridine (3) as main product, together with a significant amount of a previously unknown by‐product. The N‐methyl, O‐acetyl‐N‐methyl, N, O‐diacetyl, N‐(4‐nitrobenzoyl), and (via N → O acyl‐migration) O‐(4‐nitrobenzoyl) derivatives of the by‐product were synthesized. By aromatization of the heteroring, 4‐phenyl‐3‐pyridinemethanol (8a) was obtained. According to these derivatives and their IR, 1H and 13C NMR spectra, the by‐product is 1,2,3,6‐tetrahydro‐4‐phenyl‐3‐pyridinemethanol (4a).

Original languageEnglish
Pages (from-to)551-559
Number of pages9
JournalChemische Berichte
Issue number2
Publication statusPublished - Jan 1 1985


ASJC Scopus subject areas

  • Chemistry(all)

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