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Report | Regular issue | Vol 22, No. 2, 1984, pp.339-344
Published online, 1st January, 1970
DOI: 10.3987/R-1984-02-0339
Synthesis of 3-Halo- and 3-Formyl-4-alkylpyridines

Daniel L. Comins,* Roy K. Smith, and Eric D. Stroud

*Department of Chemistry abd Biochemistry, Utah State University, Logan, Utah 84332-0300, U.S.A.


In the presence of a catalytic amount of cuprous iodide, the addition of Grignard reagents to the 1-phenoxycarbonyl salts of 3-halopyridines gives 4-alkyl-3-halo-1-phenoxycarbonyl-1,4-dihydropyridines. The crude dihydropyridines were aromatized with o-chloranil to give 4-alkyl-3-halopyridines. Several 4-alkylnicotinaldehydes were synthesized in a similar manner from the cyclic acetal (1,3-dioxolane) of 3-pyridinecarboxaldehyde. After aromatization with sulfur, the crude acetals were hydrolyzed with oxalic acid to give the desired pyridinecarboxaldehydes.