Description
2-Amino-6-chloro-3-nitropyridine is a cytotoxic drug that has been shown to have anti-viral potency, as well as antiviral activity in an activity test. It is synthesized by reacting hydrogen tartrate with oxadiazole, and then hydrolyzing the resulting product with chloride. 2-Amino-6-chloro-3-nitropyridine has also been shown to inhibit human immunodeficiency virus type 1 (HIV) replication in vitro and to be effective against other viruses such as type 2 influenza. This drug can bind to the viral envelope and inhibit fusion of the viral membrane with host cells by preventing the release of viral contents into the cytoplasm. The binding affinity of 2-amino 6-chloro 3 nitropyridine for chloride may be due to hydrogen bonding interactions.
Uses
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.
Synthesis
The 2-Amino-6-chloro-3-nitropyridine may be obtained by the ammonolysis of 2,6-dichloro-3-nitropyridine by a known process. The ammonolysis is carried out by using solution of aqueous ammonia in methanol at 35°–40° C. After the reaction is over, the product is obtained by filtration.
References
[1] Patent: CN103936766, 2016, B. Location in patent: Paragraph 0034-0035
[2] Patent: US2015/152057, 2015, A1. Location in patent: Paragraph 0111; 0112; 0113
[3] Patent: WO2009/27732, 2009, A1. Location in patent: Page/Page column 69-70
[4] Patent: WO2004/2986, 2004, A2. Location in patent: Page 127-128
[5] Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 11.1, p. 2420 - 2429
