Extracurricular laboratory: Synthetic route of Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate

According to the analysis of related databases, 64119-42-2, the application of this compound in the production field has become more and more popular.

Synthetic Route of 64119-42-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 64119-42-2, name is Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

(a) 1-[3-Cyano-5-(ethoxycarbonyl)-6-methylpyridine-2-yl]azetidine-3-carboxylic acid Ethyl 6-chloro-5-cyano-2-methylnicotinate (50.98 g, 227 mmol), azetidine-3-carboxylic acid (24.09 g, 238 mmol) and DIPEA (118.9 mL, 681 mmol) were suspended in EtOH (250 mL) and heated at reflux for 1 h. The reaction mixture was cooled to r.t and added drop-wise to KHSO4 (154.5 g, 1135 mmol) in water (3000 mL). The solids were collected by filtration and dried under vacuum to afford 1-[3-Cyano-5-(ethoxycarbonyl)-6-methylpyridine-2-yl]azetidine-3-carboxylic acid as a solid, which was used without further purification. Yield: 65.33 g (100%). 1H NMR (400 MHz, CDCl3): delta 1.37 (3H, t, J=7.1 Hz), 2.72 (3H, s), 3.59-3.68 (1H, m), 4.31 (2H, q, J=7.1 Hz), 4.55-4.68 (4H, m), 8.28 (1H, s). MS m/z: 290 (M+1).

According to the analysis of related databases, 64119-42-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2007/244088; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem