Nicotinonitrile or 3-cyanopyridine is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula NCC₅H₄N. The molecule consists of a pyridine ring with a

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...

group attached to the 3-position. A colorless solid, it is produced by

ammoxidation In organic chemistry, ammoxidation is a process for the production of nitriles () using ammonia () and oxygen (). It is sometimes called the SOHIO process, acknowledging that ammoxidation was developed at Standard Oil of Ohio. The usual substrat ...

3-methylpyridine 3-Methylpyridine or 3-picoline, is an organic compound with formula 3-CH3C5H4N. 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 colorles ...

: :H₃CC₅H₄N + NH₃ + 1.5 O₂ → NCC₅H₄N + 3 H₂O Nicotinonitrile is a precursor to the vitamin

niacin Niacin, also known as nicotinic acid, is an organic compound and a form of vitamin B3, an essential human nutrient. It can be manufactured by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a variet ...

Nitrilase Nitrilase enzymes (nitrile aminohydrolase; ) catalyse the hydrolysis of nitriles to carboxylic acids and ammonia, without the formation of "free" amide intermediates. Nitrilases are involved in natural product biosynthesis and post translational mo ...

-catalyzed hydrolysis of 3-cyanopyridine by means of immobilized ''

Rhodococcus rhodochrous ''Rhodococcus rhodochrous'' is a bacterium used as a soil inoculant in agriculture and horticulture. It is gram positive, in the shape of rods/cocci, oxidase negative, and catalase positive. It is industrially produced to catalyse acrylonitri ...

'' J1 strains leads in quantitative yield to nicotinamide (vitamin B₃). The enzyme allows for a more selective synthesis as further hydrolysis of the amide to

nicotinic acid Niacin, also known as nicotinic acid, is an organic compound and a form of vitamin B3, an essential human nutrient. It can be manufactured by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a variet ...

is avoided. Oxidation of 3-cyanopyridine with hydrogen peroxide gives 3-cyanopyridine N-oxide, which hydrolyzes to

nicotinic acid N-oxide Nicotinic acid ''N''-oxide is an organic compound with the formula (HO2C)C5H4NO. It is the ''N''-oxide of nicotinic acid ((HO2C)C5H4N). It is prepared by oxidation of nicotinic acid or the hydrolysis of 3-cyanopyridine ''N''-oxide. The compou ...

, a precursor to pharmaceuticals.

References

{{Reflist 3-Pyridyl compounds Aromatic nitriles