30078-65-0Relevant articles and documents
Dehydration of Amides to Nitriles over Heterogeneous Silica-Supported Molybdenum Oxide Catalyst
Nagasaki, Yo-hei,Nakagawa, Yoshinao,Tamura, Masazumi,Tomishige, Keiichi,Yabushita, Mizuho
, (2022/03/15)
Silica-supported molybdenum oxide (MoOx/SiO2) with 4.8 wt% Mo (0.5 mmol g?1) was an effective and reusable heterogeneous catalyst for dehydration of 2-furamide to 2-furonitrile (96 % yield). The catalyst was applicable to
An Efficient Synthesis of Nitriles from Aldoximes in the Presence of Trifluoromethanesulfonic Anhydride in Mild Conditions
Uludag, N.
, p. 1640 - 1645 (2020/10/22)
Abstract: A new and convenient protocol has been proposed for the transformation of aldoximes to nitriles using trifluoromethanesulfonic anhydride and triethylamine. The proposed method allows a range of aldoximes, including aromatic, heterocyclic, aliphatic, and cycloaliphatic aldoximes, to be converted to the corresponding nitriles in good to excellent yields.
Direct Synthesis of Nitriles from Carboxylic Acids Using Indium-Catalyzed Transnitrilation: Mechanistic and Kinetic Study
Vanoye, Laurent,Hammoud, Ahmad,Gérard, Hélène,Barnes, Alexandra,Philippe, Régis,Fongarland, Pascal,De Bellefon, Claude,Favre-Réguillon, Alain
, p. 9705 - 9714 (2019/10/14)
Aliphatic and aromatic carboxylic acids can be quantitatively converted to the corresponding nitriles in the presence of catalysts using acetonitrile both as a solvent and reactant at 200 °C. This transformation is based on the acid-nitrile exchange (i.e., transnitrilation) and uses a nontoxic and water resistant catalyst, indium trichloride (InCl3). The mechanism of the transnitrilation was investigated both experimentally and computationally and compared to the previously proposed mechanism. In contrast to the usually assumed formation of amide as an intermediate, transnitrilation is an equilibrium reaction and proceeds via an equilibrated Mumm reaction with the formation of an imide as an intermediate. A simple and reversible mechanism was proposed for this reaction, which was validated by kinetics measurement and by density functional theory calculations of the reaction intermediates and reaction mechanisms.
O-BENZENESULFONYL-ACETOHYDROXAMIC ACID ESTER DERIVATIVE AND MANUFACTURING METHOD OF NITRYL COMPOUND
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Paragraph 0033; 0035-0037, (2017/10/26)
PROBLEM TO BE SOLVED: To provide a novel synthetic agent for manufacturing a nitryl compound without using a hydroxylamine derivative which has problems in storage property or handleability. SOLUTION: There is related O-benzene sulfonyl-acetohydroxamic acid ester derivative represented by the following chemical formula, where R1 is H, CF3 or CH3, R2 is CH3, C2H5 or C3H7. There is related a nitryl compound synthesizing agent for synthesizing a nitryl compound from an aldehyde compound containing the O-benzene sulfonyl-acetohydroxamic acid ester derivative and further a manufacturing method of a nitryl compound including a process for transferring the aldehyde compound to oxime in the presence of the synthesizing agent, an organic solvent and an acid catalyst. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
Improving Robustness: In Situ Generation of a Pd(0) Catalyst for the Cyanation of Aryl Bromides
Coombs, John R.,Fraunhoffer, Kenneth J.,Simmons, Eric M.,Stevens, Jason M.,Wisniewski, Steven R.,Yu, Miao
, p. 7040 - 7044 (2017/07/17)
Conditions have been developed for the palladium-catalyzed cyanation of aryl bromides utilizing the air-stable XantPhos-PdCl2 precatalyst. By employing a trialkylamine as a reducing agent, the active Pd(0) species is generated in situ, alleviating the need to employ the air-sensitive Pd2(dba)3. Twenty-two substituted benzonitriles have been synthesized using this method.
Half-Sandwich Guanidinate-Osmium(II) Complexes: Synthesis and Application in the Selective Dehydration of Aldoximes
Francos, Javier,González-Liste, Pedro J.,Menéndez-Rodríguez, Lucía,Crochet, Pascale,Cadierno, Victorio,Borge, Javier,Anti?olo, Antonio,Fernández-Galán, Rafael,Carrillo-Hermosilla, Fernando
, p. 393 - 402 (2016/02/03)
The novel guanidinate-osmium(II) complexes [OsCl{κ2-(N,N′)-C(NR)(NiPr)NHiPr}(η6-p-cymene)] [R = Ph (3a), 4-C6H4F (3b), 4-C6H4Cl (3c), 4-C6H4CF3 (3d), 3-C6H4CF3 (3e), 3,5-C6H3(CF3)2 (3f), 4-C6H4CN (3g), 4-C6H4Me (3h), 3-C6H4Me (3i), 2-C6H4Me (3j), 4-C6H4tBu (3k), 2,6-C6H3iPr2 (3l), 2,4,6-C6H2Me3 (3m)] have been synthesized in high yields (70-88 %) by treatment of THF solutions of the dimeric precursor [{OsCl(μ-Cl)(η6-p-cymene)}2] (1) with 4 equivalents of the corresponding guanidine (iPrHN)2C=NR (2a-m) at room temperature. The easily separable guanidinium chloride salts [(iPrHN)2C(NHR)]Cl (4a-m) were also formed in these reactions. The structures of 3a, 3d, and 3h were unequivocally confirmed by X-ray diffraction methods. Complexes 3a-m proved to be active in the catalytic dehydration of aldoximes. The best results were obtained with [OsCl{κ2-(N,N′)-C(N-4-C6H4CF3)(NiPr)NHiPr}(η6-p-cymene)] (3d; 5 mol-%), which, in acetonitrile at 80C, was able to convert selectively a large variety of aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes into the corresponding nitriles in high yields and short reaction times. Novel osmium(II)-guanidinate complexes of general composition [OsCl{κ2-(N,N′)-C(NR)(NiPr)NHiPr}(η6-p-cymene)] (R = Ar) have been synthesized and successfully employed as catalysts for the selective conversion of aldoximes into nitriles.
Ruthenium-catalyzed one-pot synthesis of primary amides from aldehydes in water
Garcia-Alvarez, Rocio,Diaz-Alvarez, Alba E.,Crochet, Pascale,Cadierno, Victorio
, p. 5889 - 5894 (2013/05/09)
The readily available arene-ruthenium(ii) complex [RuCl2(η 6-C6Me6){P(NMe2)3}] (5 mol%) proved to be an efficient catalyst for the direct synthesis of primary amides from aldehydes and hydroxylamine hydrochloride (NH2OH· HCl) in water at 100 °C. The process, which requires the presence of NaHCO3 to catch the HCl released during the formation of the key aldoxime intermediates, was operative with both aromatic, heteroaromatic, α,β-unsaturated and aliphatic aldehydes, and tolerated several functional groups. A greener approach using commercially available NH 2OH solution (50 wt.% in water) is also presented.
Direct preparation of nitriles from carboxylic acids in continuous flow
Cantillo, David,Kappe, C. Oliver
, p. 10567 - 10571 (2013/11/06)
A continuous-flow protocol for the preparation of organic nitriles from carboxylic acids has been developed. The method is based on the acid-nitrile exchange reaction with acetonitrile, used as the solvent, and takes place without any catalyst or additives under the high-temperature/high-pressure conditions employed. At 350 C and 65 bar, where acetonitrile is in its supercritical state, the transformation of benzoic acid to benzonitrile requires 25 min. The protocol has been tested for a variety of nitriles, including aromatic and aliphatic substrates.
A one-pot conversion of carboxylic acids into nitriles catalysed by PEG400 under microwave irradiation
Cao, Yu-Qing,Qu, An-Li,Liu, Rui-Yan,Duan, Chun-Ming
experimental part, p. 414 - 415 (2010/12/19)
A new efficient method for the synthesis of nitriles is reported. Carboxylic acids were converted into nitriles by a onepot reaction with hydroxylamine sulfate and zinc catalysed by PEG400 under microwave irradiation in excellent yields. The most suitable condition was 20 minutes under the microwave power of 231 W with 5 mol% PEG400.
Process for catalytically preparing aromatic or heteroaromatic nitriles
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Page/Page column 3, (2009/04/24)
The present invention relates to a process for preparing optionally substituted aromatic or heteroaromatic nitriles starting from haloaromatics. These are reacted in a copper-catalysed reaction with potassium hexacyanoferrate(II) or potassium hexacyanoferrate(III) in the presence of heteroaromatic amines.
