With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.113118-82-4, name is 5-Chloronicotinaldehyde, molecular formula is C6H4ClNO, molecular weight is 141.5551, as common compound, the synthetic route is as follows.COA of Formula: C6H4ClNO
General procedure: Oleanolic acid analogues 4e29 were obtained from Scheme 1.Firstly, oleanolic acid (0.66 mmol) and selectfluor (1-chloromethy l-4-fluoro-1, 4-diazoniabicyclo [2.2.2] octane bis (tetrafluoroborate))(1.98 mmol) were dissolved in the mixed solution of anhydrousdioxane (4 mL) and nitromethane (6 mL), and stirred at 80 C for4 h. Then the reaction mixture was concentrated under reducedpressure, extracted with ethyl acetate and deionized water, filteredand dried with anhydrous magnesium sulfate. Next, the crudeproduct was purified on a silica gel column with petroleum ether/ethyl acetate (v/v 5:1) as the eluent to obtain the intermediate OA-F.Secondly, OA-F (0.51 mmol) was added into 75 mL of acetone andstirred at 0 C until it was completely dissolved. Then the Jonesreagent (0.5 mL) was slowly added into the solution and stirred for5 min. After pretreatment similar with OA-F, the crude product waspurified via dichloromethane/petroleum ether (v/v 2:1/3:1) asthe eluent on silica gel column to produce another intermediateOA-F-01. Finally, OA-F-01 (0.44 mmol) and potassium hydroxide(0.88 mmol) were dissolved in the mixed solution of dichloromethane(10 mL) and ethanol (10 mL) followed by adding aldehyde(0.88 mmol) and stirring at room temperature for 12 h. After pretreatmentsimilar with OA-F and OA-F-01, petroleum ether/dichloromethane or ethyl acetate were used as the eluent to purifythe crude product for gaining the analogues 4-29.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-82-4, 5-Chloronicotinaldehyde, and friends who are interested can also refer to it.
Reference:
Article; Zhong, Ying-Ying; Chen, Hui-Sheng; Wu, Pan-Pan; Zhang, Bing-Jie; Yang, Yang; Zhu, Qiu-Yan; Zhang, Chun-Guo; Zhao, Su-Qing; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 706 – 716;,
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