6-Chloronicotinoyl chloride

Uses

6-Chloronicotinoyl chloride serves as an acylating agent for synthesizing N-(6-chloronicotinoyl)-β-aminobutyric acid via Schotten–Baumann reaction with β-aminobutyric acid and NaOH at –7 to –5°C, yielding the product in over 60% yield[1]. The reagent acylates steroidal substrates, including 3β,5α,6β-trihydroxysteroids, 3β,5-dihydroxy-6-ketosteroids, and 20-hydroxyecdysone (in pyridine at room temperature), to produce new esters containing 6-chloropyridine groups[2][3].

Synthesis

6-Chloronicotinoyl chloride is prepared by reacting 6-methoxynicotinic acid with thionyl chloride in refluxing DMF, followed by vacuum distillation to afford the product in high yield[2].

References

[1]Kovganko, N. V., Sokolov, S. N., & Chernov, Y. G. (2011). Synthesis of α-chloropyridine derivatives of γ-aminobutyric acid. Chemistry of Natural Compounds, 47(5), 781–782. https://doi.org/10.1007/s10600-011-0057-4
[2]Kovganko, N. V., Chernov, Y. G., Sokolov, S. N., Kashkan, Z. N., & Survilo, V. L. (2009). Synthesis of 6-chloronicotinates of steroidal 3β,5α,6β-triols and 3β,5-dihydroxy-6-ketones. Chemistry of Natural Compounds, 45(2), 200–204. https://doi.org/10.1007/s10600-009-9265-6
[3]Bobaev, I. D., Kovganko, N. V., Chernov, Y. G., Utaeva, Z. R., Sokolov, S. N., Kashkan, Z. N., & Ramazanov, N. S. (2009). Synthesis of 20-hydroxyecdysone 6-chloronicotinates. Chemistry of Natural Compounds, 45(3), 385–388. https://doi.org/10.1007/s10600-009-9338-6