40188-44-1Relevant articles and documents
Beta receptor blocker Acebutolol intermediate synthesized by photochemical Fries rearrangement
-
Paragraph 0025-0026; 0028-0029; 0031-0032; 0034-0035..., (2021/10/27)
The invention belongs to the field of organic photochemistry and medicinal chemistry, and particularly relates to a beta receptor blocker Acebutolol intermediate synthesized by photochemical Fries rearrangement. An efficient continuous acetylation synthesis method is adopted, raw materials including p-aminophenol and n-butyric anhydride are mixed and subjected to a water diversion reaction with a water-carrying agent, then the water-carrying agent is removed through distillation, reactants are cooled, water is added as a dispersing agent, then liquid caustic soda is added for a reaction, phenate is generated, acetic anhydride is dropwise added, the mixture is stirred for a reaction, ester is generated, recrystallizing is carried out to generate a first-step product N-(4-acetoxyphenyl) butyrylamide; and in the step 2 photochemical Fries liquid phase rearrangement reaction is adopted, the product in the first step is dissolved in an organic solvent, then Fries rearrangement is carried out by irradiation of ultraviolet-visible light with a specific wavelength, the solvent is heated and evaporated after the reaction is completed, and the important intermediate 2-acetyl-4-n-butyryl aminophenol of Acebutolol is obtained after recrystallization. The method is simple and easy to implement, and low-toxicity, efficient and cheap green chemical reagents are used in the synthesis process.