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3-Methylpyridine or 3-picoline, is an organic compound with formula 3-CH 3 C 5 H 4 N. It is one of three positional isomers of methylpyridine, whose structures vary according to where the methyl group is attached around the pyridine ring. This colorless liquid is a precursor to pyridine derivatives that have applications in the pharmaceutical ...
The structure of niacin, and thus β–picoline, was determined in 1883 when the Czech-Austrian chemist Zdenko Hans Skraup and Albert Cobenzl repeatedly oxidized β–naphthoquinoline and found niacin among the products, thus proving that β–picoline was 3-methylpyridine. [16]
2-Picoline was the first pyridine compound reported to be isolated in pure form. It was isolated from coal tar in 1846 by T. Anderson. [2] This chemistry was practiced by Reilly Industries. [3] It is now mainly produced by two principal routes. One method involves the condensation of acetaldehyde and ammonia in the presence of an oxide catalyst ...
4-Methylpyridine is the organic compound with the formula CH 3 C 5 H 4 N. It is one of the three isomers of methylpyridine. This pungent liquid is a building block for the synthesis of other heterocyclic compounds. Its conjugate acid, the 4-methylpyridinium ion, has a pK a of 5.98, about 0.7 units above that of pyridine itself. [1]
NC 5 H 4 CH 3 + 1.5 O 2 + NH 3 → NC 5 H 4 C≡N + 3 H 2 O NC 5 H 4 C≡N + 2 H 2 O → NC 5 H 4 CO 2 H + NH 3. It is also produced by oxidation of picoline with nitric acid. [2] In the laboratory, picolinic acid is formed from 2-methylpyridine by oxidation with potassium permanganate (KMnO 4). [3] [4]
Niacin is prepared by hydrolysis of nicotinonitrile, which, as described above, is generated by oxidation of 3-picoline. Oxidation can be effected by air, but ammoxidation is more efficient. In the latter process, nicotinonitrile is produced by ammoxidation of 3-methylpyridine .
2-methylglutaronitrile can be converted to 3-methylpyridine (β-picoline) by partial hydrogenation. [7] [8]3-Methylpyridin aus 2-MGN. In addition to 3-methylpyridine, 3-methylpiperidine is obtained as a by-product from which further 3-methylpyridine can be obtained by dehydrogenation.
Nicotinonitrile or 3-cyanopyridine is an organic compound with the formula NCC 5 H 4 N. The molecule consists of a pyridine ring with a nitrile group attached to the 3-position. A colorless solid, it is produced by ammoxidation of 3-methylpyridine: [2] H 3 CC 5 H 4 N + NH 3 + 1.5 O 2 → NCC 5 H 4 N + 3 H 2 O. Nicotinonitrile is a precursor to ...