2-Hydrazinopyridine

Chemical Properties

White to light beige low melting solid

Uses

• Enhanced Metal Removal: Utilizing Schiff base functionalized dialdehyde starch, derived from 2-hydrazinopyridine, demonstrated significant potential in enhancing the removal of Cu(II) from solutions. The study included preparation methodologies, performance evaluations, and DFT calculations, showcasing its efficacy in water treatment technologies (Liang et al., 2024).
• Dual Sensing Probe Development: A novel dicyanisophorone-based probe, incorporating 2-hydrazinopyridine, was developed for the dual sensing of Zn(2+) and Cd(2+) via near-infrared fluorescence. This advancement aids in the detection and analysis of heavy metals in various environmental and biological samples (Yan et al., 2023).
• Active Site Analysis in Lysyl Oxidase: The study provided insights into the spatial arrangement of active site components in Lysyl Oxidase-like 2, including the role of 2-hydrazinopyridine, which is critical for understanding the enzyme′s mechanism and potential therapeutic applications (Meier et al., 2022).
• Structural Analysis of Lysyl Oxidase: Research focused on the predicted 3D structure of the amine oxidase domain of Lysyl Oxidase-Like 2, exploring the interaction dynamics facilitated by 2-hydrazinopyridine. This contributes significantly to the field of molecular biology and enzyme function analysis (Meier et al., 2022).

Synthesis Reference(s)

Journal of Medicinal Chemistry, 28, p. 1394, 1985 DOI: 10.1021/jm00148a004

Synthesis

109-09-1

4930-98-7

General procedure for the synthesis of 2-hydrazinopyridine from 2-chloropyridine: To a solution of hydrazine hydrate (200 mL, 10 vol) of 2-chloropyridine (20 g, 0.176 mol, 1 eq.), the reaction was stirred for 48 hours at 100 °C. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding reagent ratio of 8:2 ethyl acetate and methanol), and after confirming that the feedstock was completely consumed, the reaction mixture was diluted with water (200 mL) and subsequently extracted with ethyl acetate (5 x 500 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to remove the solvent to afford the target product 2-hydrazinopyridine (15.0 g, 78% yield) as a red oil. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 8.14 (1H, d, J = 3Hz, Ar-H), 7.51-7.45 (1H, m, Ar-H), 6.71-6.66 (2H, m, Ar-H), 5.78 (1H, brs, -NH), 3.81 (2H, brs, -NH2).LCMS ANALYSIS: The calculated value of C5H7N3[M+H]+ was 109.13 and the measured value was 110.1.

Purification Methods

Purify it by distillation under a vacuum and by recrystallisation from Et2O/hexane. [Kauffmann et al. Justus Liebigs Ann Chem 656 103 1962, Potts & Burton J Org Chem 31 251 1966.] The mono-hydrochloride has m 183o(dec) from aqueous HCl, and the di-hydrochloride has m 214-215o. [Beilstein 22 II 487, 22 III/IV 7025, 22/14 V 486.]

References

[1] Synthetic Communications, 2011, vol. 41, # 6, p. 925 - 938
[2] Asian Journal of Chemistry, 2017, vol. 29, # 9, p. 1920 - 1924
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 23, p. 5064 - 5069
[4] Patent: EP1380296, 2004, A1
[5] Tetrahedron Letters, 2014, vol. 55, # 52, p. 7198 - 7202