Pyridine-2-carboximidamide hydrochloride

Chemical Properties

White solid

Uses

Pyridine-2-carboximidamide hydrochloride serves as a reactant in the synthesis of 1,4-bis[2,6-bis(2-pyridyl)pyrimidin-4-yl]benzene (L1), reacting with 1,4-bis[3-(pyridine-2-yl)propene-1-one]phenylene in ethanol with potassium hydroxide under reflux[6]. As a monoamidine ligand additive, pyridine-2-carboximidamide hydrochloride is incorporated into perovskite precursor solutions to passivate defect sites in the perovskite film[7].

Synthesis

General procedure for the synthesis of 2-amidinopyridine hydrochloride from 2-cyanopyridine: 2-cyanopyridine (26.01 g) was reacted with sodium methanol solution at room temperature with stirring for 22 h. Subsequently, ammonium chloride (28.01 g) was added and the reaction was continued for 6 h. The reaction was completed by filtration. After completion of the reaction, the unreacted ammonium chloride was removed by filtration. The filtrate was dried by rotary evaporator to remove the solvent and the resulting residue was washed with methanol to give a light yellow solid powder. It was further washed three times with ether to remove unreacted 2-cyanopyridine. Finally, recrystallization was carried out using mixed ethanol-ether solvent to give 2-amidinopyridine hydrochloride (Compound 2) as a white solid product. Yield: 83%.

References

[1] Patent: CN105399775,  2016,  A. Location in patent: Paragraph 0026-0028
[2] Patent: CN103936795,  2016,  B. Location in patent: Paragraph 0032-0035
[3] Bioorganic and Medicinal Chemistry,  2013,  vol. 21,  # 9,  p. 2600 - 2617
[4] Patent: WO2011/130908,  2011,  A1. Location in patent: Page/Page column 53
[5] Patent: WO2011/133444,  2011,  A1. Location in patent: Page/Page column 52
[6]Pai, S., Moos, M., Schreck, M. H., Lambert, C., & Kurth, D. G. (2017). Green-to-Red Electrochromic Fe(II) Metallo-Supramolecular Polyelectrolytes Self-Assembled from Fluorescent 2,6-Bis(2-pyridyl)pyrimidine Bithiophene. Inorganic Chemistry, 56(3), 1418–1432. https://doi.org/10.1021/acs.inorgchem.6b02496
[7]Li, K., Zhang, Z., Zhao, X., Wang, T., Li, Z., Zhang, H., Li, D., Li, F., Zhai, Y., Wang, H., Zhu, X., Chen, C., Chen, J., & Zhu, T. (2025). Dual‐Ligand Regulation of Homogeneous Cation–Anion Distribution Enables Efficient and Stable Perovskite Solar Cells. Angewandte Chemie International Edition, 64(49). https://doi.org/10.1002/anie.202518592