1072-98-6Relevant articles and documents
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.
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.
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.
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.