A. Transfer nitration of aromatics with N-nitropyridinium and quinolinium ions. ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:SIKKEMA, DOETZE JAKOB;REEL/FRAME:009226/0230, MAGELLAN SYSTEMS INTERNATIONAL LLC, MARYLAND, ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:AKZO NOBEL N.V.;REEL/FRAME:013782/0266, E. I. A Systematic Investigation on the Preparation of 2, 6-Diamino-3, 5-Dinitropyridine. Moving towards Nitrogen-Based Lewis Acids: A Theoretical Study. Stable N-acyl pyridinium and benzpyridinium salts as alkylating agents. https://doi.org/10.1016/bs.aihch.2015.03.001. ICT (1993), 24th (Energetic Materials: Insensitivity and Environmental Awareness), 6-1/6-8, DADNP is made by nitrating DAP with nitric acid and concentrated sulfuric acid in a number of steps. A. Onishchenko, T. V. Ternikova, O. Acidity and reactivity of trifluoromethanesulfonic acid in liquid and solid acid catalysts. H. H. Licht et al., Novel Explosives: Dinitropyridines , Nit. According to the present invention, it is possible to use oleum as commercially available. N. N. Makhova, G. A. Karpov, A. N. Mikhailyuk, A. E. Bova, L. I. Khmel'nitskii, S. S. Novikov. H. Ritter et al., Synthesis and Reactions of Dinitrated Amino and Diaminopyridines , J. Heterocyclic Chem., 32 (Mar. 4, 310,671 discloses the nitration of 2,6-dichloropyridine in oleum. Reaction of N-nitropyridinium salts with salts of nitro- and polynitroalkanes. By the term "pyridine-2,6-diamines" are meant 2,6-diaminopyridine (DAP) and derivative compounds with substitution in the pyridine ring of either or both amino groups and/or carbon atom no. When lower concentrations of nitric acid are used, it is preferred to employ oleum having a high sulfur trioxide content. No. * Derwent Patent Abstract No. Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. Radoslaw R Bak, Andrew J Smallridge. Synthesis of Furoxans (1,2,5-oxadiazole 2-oxides) from Styrenes and Nitrosonium Tetrafluoroborate in Non-Acidic Media and Mechanistic Study. AKZO NOBEL NV, NETHERLANDS, Free format text: Ilya V. Kuchurov, Igor V. Fomenkov, Sergei G. Zlotin, Vladimir A. Tartakovsky. Introduction Nitration of pyridine and its simple C-alkyl derivatives at a ring carbon atom with nitric acid, nitric acidsulfuric acid mixtures, or other common nitrating systems, generally results in a very low yield of nitropyridine and is of little synthetic value.1 Thus, many simple nitropyridines, which are synthetic precursors of potential pharmaceutical and agrochemical importance,27 are not available by conventional direct nitration of the parent pyridine. DOI: 10.1016/S1381-1169(01)00199-6. Moreover, the 2,6-dichloropyridine nitration is achieved only with difficulty, so it is not surprising that, in general, a powerful nitrating agent is selected. Please enable JavaScript Tetrahedron Letters 1997, 38 (32) , 5647-5650. DOI: 10.1039/b413285h. Conf. The nitration reaction of Example 1 was performed in a 1-liter reactor at 1/3 scale (somewhat shorter times were needed because of the larger specific cooling area) using ice-water cooling. You have to login with your ACS ID befor you can login with your Mendeley account. XX is the XXth reference in the list of references. Copyright © 2015 Elsevier Inc. All rights reserved. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). A Method for Heteroaromatic Nitration Demonstrating Remarkable Thermal Stability. For reproduction of material from all other RSC journals and books: For reproduction of material from all other RSC journals. Synthesis of 14C-labelled compounds. Copyright © 2020 Elsevier B.V. or its licensors or contributors. Unlimited viewing of the article/chapter PDF and any associated supplements and figures. It should be noted that this yield of 82.5% in the synthesis indicates the presence of virtually all of the theoretical amount of nitration product in the reaction mixture. In the case of DAP this option is not at all obvious, given that the dinitration as such proceeds easily and the low yield cannot be explained just like that either. Please check your email for instructions on resetting your password. Owner name: Preparation ... By Nitration of Substituted Pyridines The nitration of 2-dimethylaminopyridine-1 -oxide under mild conditions gives 2-dimethylamino-5-nitropyridine-1-oxide; significantly, none of the 4-nitro isomer is formed in the reaction.'
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