6-Aminopyridine-3-carboxylic acid (6-Aminonicotinic acid) was used in the preparation of resin-bound 2-aminoazine.
ChEBI: An aminonicotinic acid in which the amino group is situated at position 6 of the pyridine ring.
6-Aminonicotinic acid is an inhibitor of bacterial DNA gyrase and topoisomerase IV. It has been shown to inhibit the growth of a number of bacteria, including E. coli K-12, with potent inhibitory activity against these enzymes. It binds to the active sites on these enzymes and prevents them from working. The detection time for 6-aminonicotinic acid is about 3 hours after exposure. It has been shown to be more potent than other inhibitors of bacterial DNA gyrase and topoisomerase IV such as 2,4-diaminopyrimidine (2,4DAP).
Electrosynthesis of 6-aminopyridine-3-carboxylic acid (6-aminonicotinic acid) by electrochemical reduction of 2-amino-5-bromo and 2-amino-5-chloropyridine in the presence of CO2 at silver electrode has been reported.
Using 2-amino-5-methylpyridine as the starting material, it was first reacted with triethylamine and acetyl chloride in dichloromethane at 30 °C for 5 h; the product was washed with water, dried and concentrated to obtain 2-acetamido-5-methylpyridine with a yield of 90%. Then, it was reacted with 30% hydrogen peroxide at 85 °C for 16 h under the catalysis of sodium dodecylbenzene sulfonate and γ-aluminum oxide; the product was washed with water, suction-filtered and dried to obtain 6-acetamidonicotinic acid with a yield of 91%. Finally, it was reacted with aqueous sodium hydroxide solution at 80 °C for 12 h, the pH was adjusted to 3 with 6 M hydrochloric acid, and the resulting solid was suction-filtered and dried to obtain 6-aminonicotinic acid with a yield of 92%.
Crystallise the acid from aqueous acetic acid. Dry it in vacuo at 70o. [Beilstein 22 III/IV 6726.]
