Methylpyridine derivatives. II. Synthesis of 2-cyanomethylpyridines was written by Suzuki, Yasuyuki. And the article was included in Pharmaceutical Bulletin in 1957.Product Details of 1620-76-4 This article mentions the following:
In general, alkyl derivatives of 2-chloropyridine (I) were heated 10 hrs. in an autoclave with the calculated amount of Na2SO3 in H2O, and the resulting alkyl derivative of Na 2-pyridinesulfonate fused (without previous isolation) with KCN over an open flame to give the corresponding alkyl derivatives of 2-cyanopyridine (II) (derivative of I used, temperature of autoclave, b.p. and m.p. of corresponding II derivative, yield given): I itself, 150-60°, b24 114-16°, -, 49.7%; 6-Me, 170-80°, b38 135-6°, m. 69-71°, 39%; 5-Me, 200-10°, b28 135-8°, m. 72-4°, 36.8%; 4-Me, 180-90°, b38 145-8°, m. 88-9°, 39.1%; 3-Me, 170-80°, b38 139-42°, m. 87-8°, 59%; 4,6-Me2, 200-10°, b16 125-30°, m. 51-2°, 32.6%; 3,6-EtMe (III), 210-20°, b32 145-51°, -, 49.7%. Similarly, the 4-Cl derivative (IV) of III heated only 3 hrs. with Na2SO3 in an autocalve at 180-200° and fused with KCN yielded 60.6% 4-cyano derivative of III, b17 107-10°; picrate, m. 123-4°. 3-Ethyl-4-nitro-6-methylpyridine 1-oxide (9.1 g.) (Berson and Cohen, C.A. 50, 9405i) in 30 cc. CHCl3 treated dropwise in the cold with 17.8 cc. AcCl, stirred an addnl. 30 min. at 50°, 8.8 cc. PCl3 added dropwise in the cold, the mixture stirred 30 min. at room temperature, warmed 1 hr. at 60-70° on a H2O bath, cooled, poured into 100 cc. ice H2O, the aqueous layer (plus the washings from the organic layer) washed with 30 cc. ether, made alk. with Na2CO3, steam-distilled, and the distillate saturated with K2CO3 and extracted with ether yielded 5.27 g. IV, b20 92-5°; picrate, m. 133-4.5°. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4Product Details of 1620-76-4).
4-Methylpicolinonitrile (cas: 1620-76-4) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Product Details of 1620-76-4