2439-77-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxybenzamide is used as a reagent in the synthesis of benzohydroxamic acids, which are potent and selective anti-hepatitis C virus (HCV) agents. These benzohydroxamic acids have shown significant promise in the development of new therapeutic strategies against HCV, a major global health concern.
In the synthesis process, 2-methoxybenzamide serves as a key intermediate, providing a versatile platform for the development of novel HCV inhibitors. The compound's reactivity and structural features make it an ideal candidate for the creation of new drugs targeting the virus, potentially leading to more effective treatments for patients suffering from hepatitis C.
Furthermore, the pharmaceutical industry may explore additional applications of 2-methoxybenzamide in the development of other therapeutic agents, given its unique chemical properties and potential for further chemical modification. This could include the synthesis of new compounds with various biological activities, such as anti-inflammatory, analgesic, or anti-cancer properties, depending on the specific needs and requirements of the industry.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic fumes of NOx.

InChI:InChI=1/C8H9NO2/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3,(H2,9,10)

Upstream product

• 21615-34-9 2-Methoxybenzoyl chloride 
• 77-78-1 dimethyl sulfate 
• 65-45-2 salicylamide 
• 67-56-1 methanol 
• 612-24-8 o-nitrobenzonitrile 
• 135-02-4 ortho-anisaldehyde 
• 562-54-9 potassium methyl sulfate 
• 606-45-1 2-methoxybenzoic acid methyl ester 
• 7664-41-7 ammonia 
• 71-43-2 benzene 
• 866999-10-2 (2-methoxy-benzoyl)-trichloroacetyl-amine 
• 7664-93-9 sulfuric acid 
• 579-75-9 2-Methoxybenzoic acid 
• 578-58-5 2-methylmethoxybenzene 

Downstream Products

• 52059-61-7 5-(2-methoxy-phenyl)-[1,3,4]oxathiazol-2-one 
• 84632-33-7 NN-di(<(2)H>methyl)-2-methoxybenzamide 
• 345928-36-1 N-(3-Hydroxy-1,3-dihydro-isobenzofuran-1-yl)-2-methoxy-benzamide 
• 92552-95-9 N-benzoyl-2-methoxy-o-anisamide 
• 554423-67-5 N-2-chloroacetyl-2-methoxybenzamide 
• 906126-80-5 (E)-2-methoxy-N-3-phenylacryloylbenzamide 
• 1318853-37-0 C₁₈H₁₆N₂O₃ 
• 2364-62-7 n-butyl o-methoxybenzoate 
• 57149-81-2 2-methoxy-N-cyclohexyl-benzamide 

Relevant academic research and scientific papers

Nano-construction of CuO nanorods decorated with g-C3N4 nanosheets (CuO/g-C3N4-NS) as a superb colloidal nanocatalyst for liquid phase C[sbnd]H conversion of aldehydes to amides

Herein, we describe an intelligent strategy to fabricate nanosheets of graphitic carbon nitride (g-C3N4) decorated with nanorods copper oxide (CuO NRs). Then, the catalytic activity of CuONRs/g-C3N4-NS was developed for the synthesis of primary amides in water. The morphology of CuO and its synergetics effect with nanosheets g-C3N4 a major role in the yield of products. Furthermore, hydroxylamine hydrochloride (NH2OH·HCl) due to availability and affordability was used as a suitable substitute for ammonia source. The findings demonstrate that this layer nanostructure is a superb catalyst for converting various derivatives of aldehyde to their corresponding amides. The current protocol can be useful criterion in the synthesis and stabilization of metal oxides and provides new insight in organic transformation.

Efficient and selective copper-grafted nanoporous silica in aqueous conversion of aldehydes to amides

The one-pot conversion of aldehydes to their corresponding primary amides has been studied using SBA-15-grafted ethylenediamine copper complexes (En-Cu). The heterogeneous catalyst could be readily isolated from the reaction mixture and reused at least 14 times without significant loss in activity. The influence of reaction parameters was studied and the conditions determining yields and selectivities, including quantity of catalyst, solvent and base, were optimized to afford amides in high yields. The structures of synthesized catalysts were investigated using different characterization techniques including Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), CHN, atomic absorption (AA), scanning electron microscopy (SEM) and transmission electron microscopy (TEM).

Uniformly dispersed copper nanoparticles onto the modified magnetically recoverable nanocatalyst for aqueous synthesis of primary amides

Magnetically recoverable and environmentally friendly Cu-based heterogeneous catalyst has been synthesized for the one-pot conversion of aldehydes to their corresponding primary amides. The Fe3O4@SiO2 nanocomposites were prepared by synthesis of Fe3O4 magnetic nanoparticles (MNPs) which was then coated with a silica shell via St?ber method. Bi-functional cysteine amino acid was covalently bonded onto the siliceous shell of nanocatalyst. The CuII ions were then loaded onto the modified surface of nanocatalyst. Finally, uniformly dispersed copper nanoparticles were achieved by reduction of CuII ions with NaBH4. Amidation reaction of aryl halides with electron-withdrawing or electron-donating groups and hydroxylamine hydrochloride catalyzed with Fe3O4@SiO2@Cysteine-copper (FSC-Cu) MNPs in aqueous condition gave an excellent yield of products. The FSC-Cu MNPs could be easily isolated from the reaction mixture with an external magnet and reused at least 8 times without significant loss in activity.

Clean synthesis of amides over bifunctional catalysts of rhodium-loaded titanosilicates

Rhodium-loaded titanosilicates were prepared and employed as efficient bifunctional catalysts in the one-pot synthesis of benzamide from benzaldehyde, hydrogen peroxide, and ammonia, which took place through a tandem reaction including ammoximation of benzaldehyde to benzaldehydeoxime and a sequential dehydration-rehydration reaction to benzamide. Various parameters that influenced the activity and product selectivity were investigated, such as crystalline topologies of the titanosilicate supports, types of transition metals, rhodium content, reaction temperature, time, solvent, and NH3/benzaldehyde molar ratio. Ti-MWW was proved to be a suitable support for loading the Rh(OH)x species. Rh(OH)x/Ti-MWWgave 84.9% of benzaldehyde conversion and 86.9% of benzamide selectivity, and it was also catalytically active for the transformation of a variety of aldehydes to the corresponding amides. The reusability of the bifunctional catalyst was also investigated. The insitu FTIR technique confirmed that the one-pot reaction included Ti-catalyzed ammoximation of benzaldehyde to the benzaldehyde oxime intermediate and sequential rhodium hydroxide related dehydration-rehydration reaction of oximes to amides.

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

Product selectivity controlled by manganese oxide crystals in catalytic ammoxidation

The performances of heterogeneous catalysts can be effectively tuned by changing the catalyst structures. Here we report a controllable nitrile synthesis from alcohol ammoxidation, where the nitrile hydration side reaction could be efficiently prevented by changing the manganese oxide catalysts. α-Mn2O3 based catalysts are highly selective for nitrile synthesis, but MnO2-based catalysts including α, β, γ, and δ phases favour the amide production from tandem ammoxidation and hydration steps. Multiple structural, kinetic, and spectroscopic investigations reveal that water decomposition is hindered on α-Mn2O3, thus to switch off the nitrile hydration. In addition, the selectivity-control feature of manganese oxide catalysts is mainly related to their crystalline nature rather than oxide morphology, although the morphological issue is usually regarded as a crucial factor in many reactions.

Aerobic oxidation of primary amines to amides catalyzed by an annulated mesoionic carbene (MIC) stabilized Ru complex

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

Supported palladium catalyzed aminocarbonylation of aryl iodides employing bench-stable CO and NH3surrogates

A simple, efficient and phosphine free protocol for carbonylative synthesis of primary aromatic amides under polystyrene supported palladium (Pd?PS) nanoparticle (NP) catalyzed conditions has been demonstrated. Herein, instead of using two toxic and difficult to handle gases simultaneously, we have employed the solid, economical, bench stable oxalic acid as the CO source and ammonium carbamate as the NH3source in a single pot reaction. For the first time, we have applied two non-gaseous surrogates simultaneously under heterogeneous catalyst (Pd?PS) conditions for the synthesis of primary amides using an easy to handle double-vial (DV) system. The developed strategy showed a good functional group tolerance towards a wide range of aryl iodides and afforded primary aromatic amides in good yields. The Pd?PS catalyst was easy to separate and can be recycled up to four consecutive runs with small loss in catalytic activity. We have successfully extended the scope of the methodology to the synthesis of isoindole-1,3-diones from 1,2-dihalobenzene, 2-halobenzoates and 2-halobenzoic acid following double and single carbonylative cyclization approaches.

Ru-based complexes as heterogeneous potential catalysts for the amidation of aldehydes and nitriles in neat water

Five novel heterogeneous mononuclear complex-anchored Ru(III) have been efficiently sono-synthesized and characterized by utilizing several analytical techniques. The assembled complexes could be utilized as effective, robust and recyclable (up to eight consecutive runs) catalysts for one-pot transformation of a vast array of nitriles and aldehydes to primary amides in H2O under aerobic conditions. Moreover, some unreported di- and tetra-amide derivatives were obtained also under the optimal conditions. The results of ICP/OES analysis demonstrated that there is no detected leaching of the recycled catalyst, which suggests the real heterogeneity of the present protocol. The present Ru-complexes exhibited superiority compared to other reported catalysts for amide preparation in terms of low catalyst load, short reaction time, low operating temperature, no hazardous additives required, and high values of TON (990) and TOF (1980 h11).

Method for preparing amide compounds by using supported metal oxide catalytic material

The invention relates to a catalyst for preparing amide compounds, and aims to provide a method for preparing amide compounds by using a supported metal oxide catalytic material. The method comprisesthe following steps: uniformly mixing a solvent, water, an organic nitrile compound and the catalytic material; performing a reaction at 50-180 DEG C for 0.5-48 h; and hydrating and converting the organic nitrile compound into the corresponding amide compounds through the catalytic hydration effect of the catalyst in the reaction process. Adsorption and activation of the catalytic material to water molecules can be effectively regulated by regulating metal components loaded on the catalytic material and a catalytic material carrier, so that important amide compounds in chemical and agricultural processes are efficiently prepared. The provided method for preparing the amide compounds is effect, and has the advantages of high atom utilization rate in the reaction process, low reaction temperature, no additional reaction assistant in the synthesis process, no generation of toxic or harmful byproducts after the reaction, and green and environment-friendly synthesis process.