719-59-5Relevant academic research and scientific papers
Preparation method of 2-amino-5-chlorobenzophenone
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Paragraph 0025-0053, (2022/01/08)
The present invention proposes a method for preparing 2-amino-5-chlorobenzophenone, comprising: Step S1, the 5-chloro-3-phenyl-2,1-benzisoxazole is mixed with a catalyst, ethyl acetate is added, stirred until dissolved, the reaction system is maintained in a hydrogen atmosphere, the reaction pressure is controlled at 1-5atm, 20-30 ° C reaction; step S2, the reaction solution obtained in step S1 is filtered and the solvent is removed, the thick is obtained, a crystalline solvent is added to the thick, and after heating and dissolving, Cooling crystallization is filtered to give 2-amino-5-chlorobenzophenone. The preparation of the opposite of the present invention compared to the prior art, the yield of the product is higher, while there are fewer impurities, the reaction conditions are relatively mild, suitable for large-scale industrial applications.
Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles
Chang, Sukbok,Kim, Dongwook,Kim, Youyoung
supporting information, p. 12309 - 12312 (2021/12/07)
Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.
One-Pot Synthesis of 2-Aminobenzophenones from 2-Alkynyl Arylazides Catalyzed by Pd and Cu Precursors
Fan, Hui,Xu, Shijie,Yang, Fan,Zhang, Xiaoxiang,Zhao, Xuechun
supporting information, p. 4555 - 4558 (2021/08/30)
We describe a novel one-pot three-step reaction of 2-alkynyl arylazides through palladium-catalyzed formation of 3-hydroxy-3-phenylindolin-2-ones followed by hydrolysis of amide bonds and copper-catalyzed decarboxylation to give 2-aminobenzophenones. This synthetic method works well with various 2-alkynyl arylazides and affords the products in moderate to good yields under mild reaction conditions.
Copper-Catalyzed Electrophilic Amination of Arylboronic Acids with Anthranils: An Access to N-Aryl-2-aminophenones
Gao, Yang,Yang, Simin,Li, Yibiao,Huo, Yanping,Huang, Zongyi,Chen, Zumin,Hu, Xiao-Qiang
, p. 10222 - 10231 (2020/09/03)
An efficient copper-catalyzed electrophilic amination strategy has been established for the rapid synthesis of N-aryl-2-aminophenones from readily available arylboronic acids/esters and anthranils. This protocol features good functional group tolerance, broad substrate scope, and operational simplicity. Moreover, a tandem C-H borylation and C-N coupling protocol has also been developed to transform simple arenes to the valuable N-aryl-2-aminophenones in one pot. Additionally, the synthetic potential of this methodology is further demonstrated by the synthesis of various useful N-heterocycles and derivatives.
Xantphos-ligated palladium dithiolates: An unprecedented and convenient catalyst for the carbonylative Suzuki–Miyaura cross-coupling reaction with high turnover number and turnover frequency
Gaikwad, Vinayak V.,Mane, Pravin A.,Dey, Sandip,Bhanage, Bhalchandra M.
, (2019/11/19)
Xantphos- and dithiolate-ligated macrocyclic palladium complexes as an efficient and stable catalyst for the carbonylative Suzuki–Miyaura cross-coupling reaction have been synthesized. The catalysts were characterized by 1H-nuclear magnetic resonance (NMR), CHNS (carbon, hydrogen, nitrogen, and sulfur) analysis, melting point analysis, and 31P-NMR spectroscopy. Several sensitive functional groups (e.g., –NO2, –F, –Cl, –Br, –NH2, and –CN) on the aromatic ring were well tolerated in the carbonylative Suzuki–Miyaura coupling reaction. The present palladium complexes produce six times higher turnover number (TON) and five times higher turnover frequency (TOF) compared with conventional homogeneous palladium precursors. Maximum TONs in the range of 105 to 106 and TOF in the range of 104 to 105 could be generated by a very low amount of catalyst loading (10–5?mol%).
One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization
Li, Quanzhe,Liu, Jiaxin,Wei, Yin,Shi, Min
, p. 2438 - 2455 (2020/01/31)
A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.
A 2 - amino -5 - chloro benzophenone (by machine translation)
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Paragraph 0027; 0028; 0029; 0030; 0031; 0032; 0033-0069, (2019/03/28)
The invention relates to the field of organic synthetic technology, in particular to a 2 - amino - 5 - chloro benzophenone synthetic method, its use to P-chloroaniline and benzoyl chloride in a Friedel-crafts acylation reaction for the preparation of 2 - amino - 5 - chloro benzophenone, however, the reaction can be carried out under natural conditions, anhydrous conditions without the strict requirements. Point of its technological scheme comprises a S1: chlorine increase with the benzoyl-chloroaniline will be uniformly mixed in to the reaction kettle; S2: in the reactor to continue to add catalyst iridium trioxide, mix, and keep the air flow smoothly; S3: the reaction kettle temperature stable, the normal reaction; S4: to the end of the reaction, to the reaction kettle adding nitric acid solution, stirring and mixing; S5: standing, to be system layered, removing the supernatant liquid; S6: a lower liquid refluxing reaction, and the crystallization treatment to get a product. (by machine translation)
Method for producing 2-amino-5-chlorodiphenylketone
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Paragraph 0027-0068, (2019/03/28)
The invention relates to the technical field of organic synthesis, in particular to a method for producing 2-amino-5-chlorodiphenylketone. The 2-amino-5-chlorodiphenylketone is prepared by enabling p-chloroaniline and benzoyl chloride to be subjected to a Friedel-Crafts acylation reaction; however, the reaction can be carried out under the natural condition, and the anhydrous condition does not need to be strictly required. The method is characterized by comprising the following steps: S1, adding the p-chloroaniline and the benzoyl chloride into a reaction kettle and mixing uniformly; S2, continuing to add a catalyst dysprosium trioxide into the reaction kettle, mixing uniformly, and keeping air flowing; S3, controlling the temperature in the reaction kettle to be stable, enabling the reaction to be carried out normally; S4, after the reaction is completed, adding a nitric acid solution into the reaction kettle, and evenly mixing; S5, standing until the system is layered, and then removing supernatant liquid; S6, enabling underlayer liquid to be subjected to a reflux reaction, and carrying out crystallization treatment to obtain the product.
Preparation method of 2-amino-5-chlorobenzophenone
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Paragraph 0026-0061; 0067-0068, (2019/02/26)
The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2-amino-5-chlorobenzophenone. The method prepares the 2-amino-5-chlorobenzophenone through Friedel-Crafts acylation between parachloroaniline and benzoyl chloride, however, the Friedel-Crafts acylation can be performed in natural conditions and does not need to strictly require anhydrous conditions. The technical scheme comprises the following points: S1, feeding parachloroaniline and benzoyl chloride into a reaction kettle and uniformly mixing; S2, continuously feeding catalyst dysprosium oxide into the reaction kettle, uniformly mixing, and keeping an air flow unobstructed; S3, controlling temperature in the reaction kettle to be stale, so as to ensure that reaction is normally operated; S4, feeding a hydrochloric acid solution into the reaction kettle after the reaction is finished, and uniformly stirring and mixing; S5, leaving the solution to stand, and removing liquid in the upper layer after a system is layered; S6, ensuring that liquid in the lower layer is subjected to reflux reaction, and performing crystallization treatment, so as to obtain a product.
Industrial production method for preparing 2-amino-5-chlorobenzophenone
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Paragraph 0022-0068, (2019/02/13)
The invention relates to the technical field of organic synthesis, and especially relates to an industrial production method for preparing 2-amino-5-chlorobenzophenone. The 2-amino-5-chlorobenzophenone is prepared by a Friedel-Crafts acylation reaction of p-chloroaniline and benzoyl chloride, and the reaction is carried out under natural conditions without the strict requirement of anhydrous conditions. The method includes the following steps: S1, adding the p-chloroaniline and benzoyl chloride into a reaction kettle, and performing uniform mixing; S2, continuously adding a catalyst yttria into the reaction kettle, performing uniform mixing, and keeping air flowing smoothly; S3, controlling the temperature in the reaction kettle to be stable in order to make the reaction carried out normally; S4, adding a hydrochloric acid solution into the reaction kettle after the reaction is completed, and performing stirring for uniform mixing; S5, standing the obtained system to layer the system,and removing the obtained upper liquid; and S6, carrying out a refluxing reaction on the above obtained lower liquid, and carrying out crystallization treatment to obtain the product.
