Chemistry of 2-aryl-substituted 3-hydroxypyridines
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A study was made of the aminomethylation of the 2-(4′-methoxyphenyl)- and 2-(4′-hydroxyphenyl)-3-hydroxypyridines.
Based on the data of the NMR and IR spectra the amino methylation of 2-(4′-methoxyphenyl)-3-hydroxypyridine is directed to theβ-pyridol ring with the initial formation of the 6-mono- and then the 4,6-bis-Mannich bases; attempts to introduce the dialkylaminomethyl group into the anisole ring proved unsuccessful.
The aminomethylation of 2-(4′-hydroxyphenyl)-3-hydroxypyridine is initially directed to the phenol ring with the formation of the ortho- and then the di-ortho- derivatives, and only after this to theβ-pyridol ring, with successive substitution in the 6 and then in the 4 position of the pyridine ring.
KeywordsMethylation Phenol Pyridine Methoxyphenyl Hydroxyphenyl
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