(2-Chloro-3-pyridinyl)methanol

Chemical Properties

Light yellow needles

Uses

(2-Chloro-3-pyridinyl)methanol serves as a precursor for the synthesis of 3-spiro-7-azaindoline derivatives[1].

Synthesis

2-Chloro-3-chloromethyl pyridine 162.8 g (content 99.5%) was added to 270 g of water, 200 g of sodium acetate was added, heated to reflux, the reflux temperature was controlled at 110 C, and the reaction was carried out for 10 h. After removing the water, as well as the sodium acetate, and the sodium chloride, 2-chloro-3-pyridine acetic acid methyl ester was obtained as 171.9 g, with a purity of 99%.

Hydrolyzed methyl 2-chloro-3-pyridineacetate in 15% sodium hydroxide solution 300 ml at 25C for 10 hours, and removed the sodium hydroxide aqueous solution to obtain 2-chloro-3-pyridinemethanol 142.5g.

References

[1] Takai, K., Inoue, Y., Konishi, Y., Suwa, A., Uruno, Y., Matsuda, H., Nakako, T., Sakai, M., Nishikawa, H., Hashimoto, G., Enomoto, T., Kitamura, A., Uematsu, Y., Kiyoshi, A., & Sumiyoshi, T. (2014). Discovery of N-substituted 7-azaindoline derivatives as potent, orally available M1 and M4 muscarinic acetylcholine receptors selective agonists. Bioorganic & Medicinal Chemistry Letters, 24(14), 3189–3193. https://doi.org/10.1016/j.bmcl.2014.04.085