1072-98-6Relevant academic research and scientific papers
Electroorganic synthesis of 6-aminonicotinic acid from 2-amino-5-chloropyridine
Ramesh Raju,Krishna Mohan,Jayarama Reddy
, p. 4133 - 4135 (2003)
A synthesis of 6-aminonicotinic acid by electrochemical hydrogenation of 5-chloro-2-nitropyridine and electrochemical carboxylation of 2-amino-5-chloropyridine at a cathode surface in the presence of sulphuric acid and carbon dioxide in a dimethylformamide (DMF) solution at an apparent current density of 10 mA/cm2 using an undivided cell with good yields is reported.
Convenient chlorination of some special aromatic compounds using N-chlorosuccinimide
Gan, Zongjie,Hu, Bin,Song, Qiao,Xu, Yungen
, p. 1074 - 1078 (2012)
Some chlorinated aromatic compounds, including indole, benzofuran, carbazole, pyridine and aniline derivatives, are difficult to obtain through convenient chlorination. We herein report their efficient synthesis through chlorination with N-chlorosuccinimide (NCS). Optimization of the reaction conditions, including the temperature and the choice of solvent, was also investigated. This approach, which is characterized by a facile procedure, comparatively high yields and environmentally friendly features, provides a straightforward and inexpensive route to several chlorinated aromatic compounds. Georg Thieme Verlag Stuttgart · New York.
Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
, (2021)
N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.
N-azinylpyridinium N-aminides: An approach to pyrazolopyridines via an intramolecular radical pathway
Nu?ez, Araceli,García de Viedma, Aránzazu,Martínez-Barrasa, Valentín,Burgos, Carolina,Alvarez-Builla, Julio
, p. 1093 - 1096 (2002)
Intramolecular radical arylation, under thermal conditions, to a π-deficient pyridinium, linked to a π-excessive 2-azinyliminopyridine moiety is described. The method allows a new entry to pyrazolo[1,5-a]pyridine nucleus.
Method for catalytic synthesis of 2-amino-5-chloropyridine by microwave synergistic lewis acidic ionic liquid
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Paragraph 0018-0020, (2020/10/14)
The invention relates to a method for catalytic synthesis of 2-amino-5-chloropyridine by microwave synergistic lewis acidic ionic liquid, which comprises the following steps: adding 2-aminopyridine asa raw material into an organic solvent, introducing chlorine under the action of a catalyst lewis acidic ionic liquid and microwave radiation, and carrying out chlorination reaction; and carrying outreduced pressure distillation on the obtained reaction solution to remove the solvent, and further recrystallizing the solution to obtain the high-purity 2-amino-5-chloropyridine. Compared with the prior art, the method has the advantages that the production process is simplified, the reaction conditions are mild, the product purity is higher, the lewis acidic ionic liquid can be recycled, and the production cost is low.
One-step high-efficient high-selective synthesis of 2 - amino -5 - chloro pyridine method (by machine translation)
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Paragraph 0023; 0024; 0025; 0026; 0027; 0028, (2019/01/23)
The invention belongs to the technical field of the synthesis of intermediates, in particular relates to a one-step high-efficient high-selective synthesis of 2 - amino - 5 - chloro pyridine method. In order to 2 - aminopyridine as raw material, in the added to the organic solvent, in the blue LED lamp irradiation, instillment bromide as a catalyst, to be solution after the fading, access chlorine, to carry out a chlorination reaction; the resulting reaction solution is distilled under reduced pressure to obtain crude, further recrystallization to obtain high-purity 2 - amino - 5 - chloro pyridine. This invention adopts the bromine as catalyst, under irradiation of the blue LED lamp, produces the bromine radical with 2 - aminopyridine ring 5 phase combination, then chlorinated, avoid direct chlorinated products caused by 2 - amino - 5 - chloro pyridine series reaction generating multi-chloro, good selectivity of chloride content at the same time higher 2 - amino - 5 - chloro pyridine. The invention compared with the existing technology, the production process is simplified, mild reaction conditions, high product purity, the production cost is low, small amount of waste water. (by machine translation)
Preparation method of 2-amino substituted six-membered nitrogen-containing heterocycle complex
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Paragraph 0025; 0026; 0081, (2019/02/08)
The invention discloses a preparation method of a 2-amino substituted six-membered nitrogen-containing heterocycle complex. The preparation method comprises the following steps: mix 2-fluorine substituted six-membered nitrogen-containing heterocycle complex and amidine hydrochloride salt compound, and then react under the action of a alkaline substance to obtain a 2-amino substituted six-memberednitrogen-containing heterocycle complex. Preferably, the 2-amino substituted six-membered nitrogen-containing heterocycle complex is a 2-amino pyridine compound, a 2-aminopyrimidine compound or a 2-aminopyrazine compound. Compared with the prior art, the method has the advantages of simple synthesis conditions, less reaction steps, mild reaction conditions, low cost of the catalyst used, less waste discharge and good functional group tolerance.
BF3·SMe2 for Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles
S?derstr?m, Marcus,Zamaratski, Edouard,Odell, Luke R.
, p. 5402 - 5408 (2019/06/27)
Herein, a general, solvent-free and straightforward thiomethylation of electron deficient heterocycles using BF3·SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3·SMe2 towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non-malodorous reagent while the discovery of novel chemical transformations using BF3·SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent.
Simple 2-amino-5-halogenated pyridine preparation method
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Paragraph 0029-0032, (2019/10/01)
The invention provides a 2-amino-5-halogenated pyridine preparation method, which comprises: carrying out an addition reaction on 4-cyano-1-butyne and a halogen element X2 in a solvent under the catalysis of an acidic catalyst to obtain 4,4,5,5-tetrahalogenated n-valeronitrile, and carrying out cyclization on the 4,4,5,5-tetrahalogenated n-valeronitrile and ammonia through pyridine to obtain 2-amino-5-halogenated pyridine. According to the present invention, the preparation method has advantages of mild preparation condition, safety, environmental protection, low cost, high selectivity, less by-products and high product yield, and is suitable for industrial production.
A 2 - amino -5 chloro pyridine preparation method (by machine translation)
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Paragraph 0033-0036; 0048-0054; 0066-0069; 0081-0084, (2018/11/03)
The invention discloses a 2 - amino - 5 chloro pyridine of the preparation method, which belongs to the technical field of pharmaceutical intermediate synthesis. The invention relates to 2 - aminopyridine as raw materials, using saturated and sodium chlorate aqueous solution is used as the reaction solvent, to TEBA as catalyst, control the reaction process Cl atoms in the slow release of the reaction to obtain 2 - amino - 5 chloro pyridine, basic without side reaction, then the methanol and activated carbon to decolorize the refined, the obtained product by chromatography, purity can be as high as 99.8% of the left and right, the invention provides a preparation method, the reaction step is simple, easy to control, does not need to ethanol and other organic reagent as a reaction reagent, has reduced the three waste discharge, and also improves the purity and quality of the product. (by machine translation)
