Nicotinonitrile Explained

Nicotinonitrile or 3-cyanopyridine is an organic compound with the formula NCC5H4N. 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:

H3CC5H4N + NH3 + 1.5 O2 → NCC5H4N + 3 H2O

Nicotinonitrile is a precursor to the vitamin niacin.[1]

Nitrilase-catalyzed hydrolysis of 3-cyanopyridine by means of immobilized Rhodococcus rhodochrous J1 strains leads in quantitative yield to nicotinamide (vitamin B3).[2] [3] [4] The enzyme allows for a more selective synthesis as further hydrolysis of the amide to nicotinic acid is avoided.[5]

Oxidation of 3-cyanopyridine with hydrogen peroxide gives 3-cyanopyridine N-oxide, which hydrolyzes to nicotinic acid N-oxide, a precursor to pharmaceuticals.

Notes and References

  1. Book: Eggersdorfer . Manfred . Adam . Geo . John . Michael . Hähnlein . Wolfgang . Labler . Ludvik . Baldenius . Kai-U. . von dem Bussche-Hünnefeld . Linda . Hilgemann . Eckhard . Hoppe . Peter . Stürmer . Rainer . Weber . Fritz . Rüttimann . August . Moine . Gérard . Hohmann . Hans-Peter . Kurth . Roland . Paust . Joachim . Hähnlein . Wolfgang . Pauling . Horst . Weimann . Bernd-Jürgen . Kaesler . Bruno . Oster . Bernd . Fechtel . Ulrich . Kaiser . Klaus . de Potzolli . Bernd . Casutt . Michael . Koppe . Thomas . Schwarz . Michael . Weimann . Bernd-Jürgen . Hengartner . Urs . de Saizieu . Antoine . Wehrli . Christof . Blum . René . Vitamins . 2000 . Wiley-VCH Verlag GmbH & Co. KGaA . 978-3527306732 . 148–150 . en. 10.1002/14356007.a27_443 .
  2. Nitrile Hydratase-Catalyzed Production of Nicotinamide from 3-Cyanopyridine in Rhodococcus rhodochrous J1. Toru. Nagasawa. Caluwadewa Deepal. Mathew. Jacques. Mauger. Hideaki. Yamada. Appl. Environ. Microbiol.. 1988. 54. 7. 1766–1769. 10.1128/AEM.54.7.1766-1769.1988. 16347686. 202743. 1988ApEnM..54.1766N. free.
  3. Book: White Biotechnology. Roland. Ulber. Dieter. Sell. Building Blocks. 105. Advances in Biochemical Engineering / Biotechnology. 9783540456957. 10.1007/10_033. 17408083. 133–173. https://books.google.com/books?id=_tXoG93OWHgC&pg=PA141. Springer Science & Business Media. 2007. Hilterhaus. L.. Liese. A..
  4. Book: Biocatalysis in Organic Synthesis 1. Science of Synthesis. Georg Thieme Verlag. 2015. Enzymatic Synthesis of Amides. J. W.. Schmidberger. L. J.. Hepworth. A. P.. Green. S. L.. Flitsch. 329–372. 9783131766113. Kurt. Faber. Wolf-Dieter. Fessner. Nicholas J.. Turner. https://books.google.com/books?id=8h_wBgAAQBAJ&pg=PA362.
  5. Biocatalysis. Michael. Petersen. Andreas. Kiener. 10.1039/A809538H. Green Chem.. 1999. 1. 2. 99–106.

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