Synthesis of 2- and 4-cyanopyridines was written by Okamoto, Toshihiko;Tani, Hideo. And the article was included in Chem. & Pharm. Bull. (Tokyo) in 1959.SDS of cas: 1620-76-4 This article mentions the following:
Addition of MeI or Me2SO4 to pyridine or quinoline N-oxides gave their quaternary salts, which were stirred 1 hr. at room temperature with KCN to give 2- and 4-cyano derivatives of pyridine or quinoline, separated by extraction with CHCl3 and either vacuum distillation or Al2O3 chromatography of the extract The compound whose N-oxide was used, % yield, m.p. (or b.p.), and m.p. of the picrate of its 4-cyano derivative, and the same data repeated for its 2-cyano derivative were: C5H5N, 25, 78-80°, 197-9°, 50, b20 110-17°, -; 2-picoline, 18, -, 164-5°, (6-cyano derivative) 45, 70-2°, -; 3-picoline, 15, -, 154-6°, 30, 85-6°, -; 4-picoline, 28, 88-91° -, -, -, -; 2,6-lutidine, 13, 80-3°, 175-8°, (6-cyanomethyl-2-picoline) 33, b22 125-33°, 176-9°; and quinoline, trace, -, 175-7°, 70, 91-5°, -. All products were identified by mixed m.p. with samples synthesized by different routes. The ratio of isomers formed depended on reaction conditions. Two mechanisms were suggested for the reaction. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4SDS of cas: 1620-76-4).
4-Methylpicolinonitrile (cas: 1620-76-4) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.SDS of cas: 1620-76-4