The origin of a common compound about Citrazinic acid

According to the analysis of related databases, 99-11-6, the application of this compound in the production field has become more and more popular.

Application of 99-11-6, 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 99-11-6, name is Citrazinic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of citrazinic acid (15 g) is added phosphorous oxybromide (45 g) and the mixture heated to 140 C. After 14 h the mixture is cooled to 0 C. and MeOH (100 ml) added carefully under vigorous stirring. The mixture is then poured into a cooled (0 C.) aqueous sodium carbonate solution (1M, 500 ml), and chloroform (500 ml) is added. The biphasic mixture is filtered and the organic layer separated. After filtering through charcoal, the solution is concentrated in vacuum. The residue is purified by MPLC (dichloromethane:MeOH 100:3 to 100:6) to yield methyl 2,6-dibromoisonicotinate (13.7 g). HPLC (Rt)=1.62 (method D). To a stirred solution of I5 (2.6 g) in dioxane (30 ml) under argon is added methyl 2,6-dibromoisonicotinate (2.2 g), palladium acetate (167 mg), Xanthphos (432 mg) and Cs2CO3 (5.6 g) and the mixture refluxed for 1 h. The mixture is allowed to cool to room temperature and then added to water and extracted with EtOAc. The organic extracts are washed with brine, dried under Na2SO4, filtered and the solvent evaporated under reduced pressure. The crude product is purified by HPLC (Method E) affording I6 (0.6 g).

According to the analysis of related databases, 99-11-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/264729; (2012); A1;,
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