1603-40-3Relevant articles and documents
Vapor pressure and enthalpy of vaporization of 2-amino-3-methylpyridine
Yuan, Xiong-Jun,Xue, Wei-Lan,Zeng, Zuo-Xiang,Pu, Tong
, p. 2431 - 2435 (2007)
The vapor pressure of 2-amino-3-methylpyridine was measured in the temperature range of (328.70 to 499.88) K using the boiling point method. The Antoine equation was used to describe the vapor pressure data, and the parameters in the equation were determined by means of the least-square regression method. The deviation of experimental data from the corresponding calculated values was within 0.30 %. On the basis of the equation, the enthalpy of vaporization of 2-amino-3-methylpyridine at normal boiling point (T b) was obtained from the slope of the plot of In p vs 1/T. The standard enthalpy of vaporization ΔvapH(298.15 K) was estimated by Othmer's method. Using 3-methylpyridine as the standard substance, the value of Δvap#(298.15 K) was found to be 62.58 kJ·mol -1. A parallel value of ΔvapH(298.15 K) was also obtained using benzene as the standard substance. Additionally the Watson relation was employed to verify the value of ΔvapH(298.15 K), from which it was shown that the value of the standard enthalpy of vaporization was acceptable.
Mild, General, and Regioselective Synthesis of 2-Aminopyridines from Pyridine N -Oxides via N -(2-Pyridyl)pyridinium Salts
Xiong, Hui,Hoye, Adam T.
supporting information, p. 371 - 375 (2022/01/27)
A synthesis of 2-aminopyridines from pyridine N-oxides via their corresponding N-(2-pyridyl)pyridinium salts has been demonstrated and investigated. The reaction sequence features a highly regioselective conversion of the N-oxide into its pyridinium salt
New synthesis method of 2-amino-3-methylpyridine
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Page/Page column 3-4, (2019/05/15)
The invention belongs to the field of organic substance synthesis and particularly relates to a new synthesis method of 2-amino-3-methylpyridine. With H2O2 being an oxidant, 2-cyano-3-methylpyridine is subjected to incomplete hydrolysis to form 3-methyl-2-pyridinecarboxamide under diluted alkali conditions; then Hofmann degradation is carried out by using fresh sodium hypobromite. The new preparation method not only is reduced in cost and protects environment, but also is simple in operation and convenient in post-treatment. The method is high in yield, is simple in synthesis and is suitable for industrial production.
Diverse Oxidative C(sp2)-N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides
Xu, Fangzhou,Wang, Yanyan,Xun, Xiwei,Huang, Yun,Jin, Zhichao,Song, Baoan,Wu, Jian
, p. 8411 - 8422 (2019/05/17)
An efficient and chemoselective C(sp2)-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some α-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.
Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters
Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.
supporting information, p. 482 - 487 (2019/01/04)
A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.
Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride
Li, Yibiao,Huang, Shuo,Liao, Chunshu,Shao, Yan,Chen, Lu
supporting information, p. 7564 - 7567 (2018/11/02)
Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products.
PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS
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Page/Page column 51; 54, (2017/04/11)
The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).
Method for preparing 2-amino-5-methylpyridine through ammoniation of 3-methylpyridine
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Paragraph 0024; 0025; 0026; 0027; 0028; 0029; 0030-0035, (2017/08/28)
The invention discloses a method for preparing 2-amino-5-methylpyridine through ammoniation of 3-methylpyridine. The method comprises the following steps: placing a solvent, metallic sodium, a catalyst, an additive and the raw material 3-methylpyridine in a high-pressure reaction container, carrying out heating to 50 to 80 DEG C, then slowly adding liquefied ammonia and carrying out pressurization for a reaction; continuing pressurization to 3 to 6 MPa and heating to 150 to 190 DEG C and continuing the reaction; and terminating the reaction until no obvious pressure increase occurs during the reaction. According to the invention, a one-pot process is employed, and hydrolysis, liquid separation and rectification are successively carried out so as to produce 2-amino-5-methylpyridine and byproduce 2-amino-3-methylpyridine, wherein a ratio of 2-amino-5-methylpyridine to 2-amino-3-methylpyridine is in a range of (9-20): 1. The method has a high 3-methylpyridine conversion rate; the selectivity of the obtained 2-amino-5-methylpyridine can reach 90% or above; and the yield of 2-amino-5-methylpyridine can be increased to 84.5% or above.
Novel ammonium ionic liquids as scavengers for aromatic and heterocyclic amines: Conversion into new pharmacological agents
Elshaarawy, Reda F.M.,Mokbel, Wafaa A.,El-Sawi, Emtithal A.
, p. 1123 - 1132 (2016/09/28)
The aim of our protocol is to develop new simple, economic and efficient scavengers for primary amines, due to their substantial adverse impacts on environment and human health. In this endeavor, we have designed, successfully synthesized and structurally characterized new salicylaldehyde-tri-nbutylammonium ionic liquids which were investigated as scavengers for diverse aromatic and heterocyclic primary amines in the synthesis of new pharmacologically relevant candidates, imines scavenging product, via Schiff-base-scavenging reaction. The new scavengers exhibited good capture efficiency and can be easily regenerated and reused. The advantages of our scavengers over polymer-supported scavengers are the simplicity, shorter reaction time and real-time monitoring of a model reaction. The biocidal and antitumor activities of the scavenging products revealed a moderate to excellent broad-spectrum antibacterial efficacy, low activity or inactivity as fungicides and different levels of cytotoxicity (weak to excellent) against human breast carcinoma (MCF-7) cells.
Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts
Cheung, Chi Wai,Surry, David S.,Buchwald, Stephen L.
supporting information, p. 3734 - 3737 (2013/08/23)
A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.
