5-Aminopyridine-2-carboxylic Acid

Chemical Properties

Plates

Uses

5-Aminopyridine-2-carboxylic Acid is a useful synthetic intermediate.

Application

5-Aminopyridine-2-carboxylic Acid can synthesize novel vanadium coordination compounds that have a mononuclear structure with crystallization water molecules in the network. This compound exhibits intense photoluminescence emission at room temperature in the solid state and shows in vivo antidiabetic activity together with low in vitro cell toxicities[1]. In addition, the functionalization of graphene oxide (GO) via chromium complexes coordinated on 5-aminopyridine-2-carboxylic acid could be used as a symmetric supercapacitor electrode material in energy storage devices[2].

Synthesis

General procedure for the synthesis of 5-amino-2-pyridinecarboxylic acid from 3-amino-6-cyanopyridine: preparation of intermediate 76.5-aminopyridine-2-carboxylic acid. 5-Amino-2-cyanopyridine (10.0 g, 83.9 mmol) was dissolved in sulfuric acid (50 mL), and the resulting solution was transferred to a high-pressure vessel and reacted at 90 °C for 2 hours. Subsequently, water (100 mL) was added to the reaction mixture and continued to be heated to 100 °C for 2 hours. Upon completion of the reaction, the orange reaction solution was slowly poured into the ice-water mixture with continuous stirring for 15 minutes, at which time a light beige solid precipitated. The solid product was collected by filtration, washed with cold water and subsequently dried under vacuum overnight to afford the target compound 5-amino-2-pyridinecarboxylic acid (11.7 g, 100% yield).LRMS (m/z): 139 (M + 1)+.

References

[1] Esteban-Parra, Gines M. , et al. "Anti-diabetic and anti-parasitic properties of a family of luminescent zinc coordination compounds based on the 7-amino-5-methyl-1,2,4-triazolo[1,5-alpha] pyrimidine ligand." Journal of Inorganic Biochemistry: An Interdisciplinary Journal 212-(2020):212.
[2] A, Mohammad Dashti Najafi , et al. "Functionalization of Graphene Oxide via chromium complexes coordinated on 5-Aminopyridine-2-carboxylic acid as a symmetric supercapacitor electrode materials in energy storage devices." Composites Science and Technology (2021).