Chemical Properties
White to off-white solid
Uses
2-Chloro-4-cyanopyridine is an intermediate used to prepare pyrrolopyridine inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). It is also used to synthesize pyridinyl-tetrazoles as scaffold to identify matrix MMP-13 inhibitors for treatment of osteoarthritis.
Materials Uses
2-Chloro-4-cyanopyridine is employed in the formulation of advanced materials, including polymers and coatings, offering improved durability and chemical resistance compared to similar compounds.
Synthesis
The general procedure for the synthesis of 2-chloro-4-cyanopyridine from 4-cyanopyridine N-oxide was as follows: 120 g of 4-cyanopyridine-N-oxide, 360 mL of 1,2-dichloroethane, and 183.6 g of phosphorochloridic acid were added sequentially in a 1000 mL three-necked reaction flask. After the reaction system was cooled to -2±2°C, 151.5 g of triethylamine was added slowly dropwise for a controlled dropwise time of 2 hours. After the dropwise addition, the reaction was continued at the same temperature with stirring for 2 hours. Upon completion of the reaction, the reaction solution was concentrated by reduced pressure distillation until no fractions flowed out. 240 mL of water was added to the concentrated solution and a large amount of solid was precipitated after thorough stirring. The solid was collected by filtration and the filter cake was washed with appropriate amount of water to obtain 117.5 g of white solid product 2-chloro-4-cyanopyridine.
References
[1] Tetrahedron Letters, 2001, vol. 42, # 39, p. 6815 - 6818
[2] Patent: CN104945383, 2017, B. Location in patent: Paragraph 0031; 0035; 0036
