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Isolation and structure elucidation of the by‐product formed in the aminomethylation of α‐methylstyrene
Author(s) -
Sohár Pál,
Lázár János,
Bernáth Gábor
Publication year - 1985
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19851180215
Subject(s) - chemistry , aromatization , product (mathematics) , diacetyl , stereochemistry , nmr spectra database , medicinal chemistry , organic chemistry , spectral line , catalysis , physics , geometry , mathematics , astronomy
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, 1 H and 13 C NMR spectra, the by‐product is 1,2,3,6‐tetrahydro‐4‐phenyl‐3‐pyridinemethanol ( 4a ).
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