2835-68-9Relevant articles and documents
The reduction of aromatic nitro groups on solid supports using sodium hydrosulfite (Na2S2O4)
Scheuerman,Tumelty
, p. 6531 - 6535 (2000)
An improved method for reducing aromatic nitro compounds on solid-phase supports using sodium hydrosulfite is presented. Conditions have been optimized to enable the use of this reagent for reductions on both polyethyleneglycol-polystyrene (PEG) resins an
Heterogeneous catalyzed reduction of polymer-bound nitroarenes
Roedel, Martin,Thieme, Florian,Buchholz, Herwig,Koenig, Burkhard
, p. 1181 - 1187 (2002)
Deposition of palladium as a catalyst on polymer beads, such as Merrifield resin or TentaGel, allows the reduction of polymer-bound 4-nitro benzoate to the corresponding anilines with dilute hydrazine hydrate solution in DMF at room temperature.
RhNPs/SBA-NH2: A high-performance catalyst for aqueous phase reduction of nitroarenes to aminoarenes at room temperature
Ganji, Saidulu,Enumula, Siva Sankar,Marella, Ravi Kumar,Rao, Kamaraju Seetha Rama,Burri, David Raju
, p. 1813 - 1819 (2014)
A RhNPs/SBA-NH2 catalyst with 2) as support, rhodium acetyl acetonate as a Rh precursor and sodium borohydride (NaBH4) as a re
Ammonium sulphate - Magnesium promoted selective reduction of aromatic nitro compounds
Prajapati,Borah,Sandhu,Ghosh
, p. 4025 - 4028 (1995)
Various nitroarenes and 2,1,3-benzooxadiazole-1-oxides were selectively and rapidly reduced to their corresponding amino and diamino compounds respectively in high yields using (NH4)2SO4-Mg/Al/Bi, a new reduction system.
Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions
Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter
, p. 133 - 146 (2021/11/04)
Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.
Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes
Fu, Lihua,Li, Dingzhong,Lu, Hao,Qiu, Renhua,Sun, Tulai,Xing, Chen,Yang, Tianbao
, (2022/01/11)
The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).
Aerobic oxidation of primary amines to amides catalyzed by an annulated mesoionic carbene (MIC) stabilized Ru complex
Yadav, Suman,Reshi, Noor U Din,Pal, Saikat,Bera, Jitendra K.
, p. 7018 - 7028 (2021/11/17)
Catalytic aerobic oxidation of primary amines to the amides, using the precatalyst [Ru(COD)(L1)Br2] (1) bearing an annulated π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand L1, is disclosed. This catalytic protocol is distinguished by its high activity and selectivity, wide substrate scope and modest reaction conditions. A variety of primary amines, RCH2NH2 (R = aliphatic, aromatic and heteroaromatic), are converted to the corresponding amides using ambient air as an oxidant in the presence of a sub-stoichiometric amount of KOtBu in tBuOH. A set of control experiments, Hammett relationships, kinetic studies and DFT calculations are undertaken to divulge mechanistic details of the amine oxidation using 1. The catalytic reaction involves abstraction of two amine protons and two benzylic hydrogen atoms of the metal-bound primary amine by the oxo and hydroxo ligands, respectively. A β-hydride transfer step for the benzylic C-H bond cleavage is not supported by Hammett studies. The nitrile generated by the catalytic oxidation undergoes hydration to afford the amide as the final product. This journal is
Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex
-
Paragraph 0015, (2021/04/17)
The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.
Preparation method of 4-aminobenzoic acid and derivatives thereof
-
Paragraph 0029; 0055-0056, (2021/05/05)
The invention discloses a preparation method of 4-aminobenzoic acid and derivatives thereof. The method comprises the following steps: (1) reacting an acid ester raw material, namely 1, 4-phthalic acid monoester or 1, 4-phthalic acid diester or 1, 4-phthalic acid monoester monoamide, with hydroxylamine to obtain a 4-carboxyl benzoyl hydroxamic acid inorganic salt, a 4-alkoxyacyl benzoyl hydroxamic acid inorganic salt and a 4-carbamoyl benzoyl hydroxamic acid inorganic salt respectively; and (2), enabling the 4-carboxyl benzoyl hydroxamic acid inorganic salt, the 4-alkoxyacyl benzoyl hydroxamic acid inorganic salt or the 4-carbamoyl benzoyl hydroxamic acid inorganic salt to be subjected to rearrangement reaction, so as to obtain the 4-aminobenzoate, the 4-aminobenzoate ester and the 4-aminobenzamide; and acidifying the 4-aminobenzoate to obtain the 4-aminobenzoic acid. Nitrification and reduction reactions are not used, and hidden dangers of waste acid pollution and explosive polynitrobenzene are eliminated.
Highly efficient hydrogenation reduction of aromatic nitro compounds using MOF derivative Co-N/C catalyst
Dai, Yuyu,Li, Xiaoqing,Wang, Likai,Xu, Xiangsheng
, p. 22908 - 22914 (2021/12/24)
The direct hydrogenation reduction of aromatic nitro compounds to aromatic amines with non-noble metals is an attractive area. Herein, the pyrolysis of Co(2-methylimidazole)2 metal-organic framework successfully produces a magnetic Co-N/C nanocomposite, which exhibits a porous structure with a high specific area and uniform Co nanoparticle distribution in nitrogen-doped graphite. In addition, the Co-N/C catalysts possess high cobalt content (23%) with highly active β-Co as the main existing form and high nitrogen content (3%). These interesting characteristics endow the Co-N/C nanocomposite with excellent catalytic activity for the hydrogenation reduction of nitro compounds under mild conditions. In addition, the obtained Co-N/C nanocomposites possess a broad substrate scope and good cycle stability for the reduction of halogen-substituted or carbonyl substituted phenyl nitrates. This journal is
