2-Aminopyridine is an organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula H₂NC₅H₄N. It is one of three isomer

Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...

ic aminopyridines. It is a colourless solid that is used in the production of the drugs piroxicam

Piroxicam

Piroxicam is a non-steroidal anti-inflammatory drug of the oxicam class used to relieve the symptoms of rheumatoid and osteoarthritis, primary dysmenorrhoea, postoperative pain; and act as an analgesic, especially where there is an inflammatory component...

, sulfapyridine

Sulfapyridine

Sulfapyridine, original UK spelling Sulphapyridine, is a sulfonamide antibacterial. At one time it was commonly referred to as M&B....

, tenoxicam

Tenoxicam

Tenoxicam is a non-steroidal anti-inflammatory drug . It is manufactured by Roche under the trade name Mobiflex. It is available in the United Kingdom as a prescription-only drug. Tenoxicam belongs to the class of NSAIDs known as oxicams...

, and tripelennamine

Tripelennamine

Tripelennamine is psychoactive drug and member of the pyridine and ethylenediamine classes that is used as an antipruritic and first-generation antihistamine...

. It is produced by the reaction of sodium amide

Sodium amide

Sodium amide, commonly called sodamide, is the chemical compound with the formula NaNH2. This solid, which is dangerously reactive toward water, is white when pure, but commercial samples are typically gray due to the presence of small quantities of metallic iron from the manufacturing process...

 with pyridine

Pyridine

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...

, the Chichibabin reaction

Chichibabin reaction

The Chichibabin reaction -chē-bā-bēn) is a method for producing 2-aminopyridine derivatives by the reaction of pyridine with sodium amide. It was reported by Aleksei Chichibabin in 1914. The following is the overall form of the general reaction:...

.

Structure

Although 2-hydroxypyridine exists in significant amounts as the pyridone tautomer

Tautomer

Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. This reaction commonly results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond...

, the related imine tautomer (HNC₅H₄NH) is less important for 2-aminopyridine.

External links

• MSDS