Method for large-scale production of alpha, alpha, alpha-terpyridyl

Abstract

The invention discloses a method for large-scale production of alpha, alpha, alpha-terpyridyl. The method adopts the following synthetic route: the reaction operation in the step a is as follows: adding 2-acetylpyridine, N, N-dimethylformamide dimethyl acetal and a catalyst into an organic solvent at room temperature, reacting under reflux, and after the reaction is finished, after cooling the reaction solution to room temperature, pouring the reaction solution into a sodium hydroxide aqueous solution, extracting a product by using dichloromethane, washing, drying and concentrating an obtained organic phase, and recrystallizing an obtained crude product to obtain an intermediate, namely 1-(3-pyridyl)-3-(dimethylamino)-2-propylene-1-ketone. The method not only is easy to realize large-scale production, but also is high in yield, low in cost, simple to operate and mild in reaction condition.

Description

technical field [0001] The invention relates to a method for large-scale production of α,α,α-terpyridine, which belongs to the technical field of organic synthesis. Background technique [0002] α,α,α-Terpyridine, its CAS number is 1148-79-4, and its chemical structure is as follows: [0003] [0004] Terpyridine was first isolated in the 1930s by Morgan and Burstall. Because terpyridine and its derivatives have R electron-donating ability and P electron-accepting ability, they can form stable complexes with various metal ions, and are widely used chelating ligands in modern coordination chemistry. The complex has good affinity with N, S-containing biomacromolecules such as protein and DNA, and the luminescent properties will change, so it can be applied to biological probes; in addition, since α,α,α-terpyridine contains Three N atoms, it can be used as a tridentate ligand to chelate with various transition metals and form stable complexes, so terpyridine has also been ...

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Problems solved by technology

[0005] At present, the method for synthesizing terpyridine is mainly the coupling method, because the coupling method needs to use tin reagent, which is more toxic, and also needs palladium catalyst, which has high cost, The post-processing is cumbersome and the metal residue is not easy to remove, so it is not suitable for large-scale production

Chinese patent document CN109096339A discloses a kind of intermediate 1-(3-pyridyl)-3-(dimethylamino)- 2-propen-1-one, and then the intermediate is combined with 2-acetylpyridine in the presence of potassium tert-butoxide to synthesize terpyridine. Although the process is carried out in two steps without precious metal catalysts, the first step needs to be reduced Pressure distillation removes xylene, which has environmental protection and energy consumption problems; and the second step reaction needs to be purified by flash column chromatography, so that the yield is only 15%; therefore it is not suitable for large-scale production requirements

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