6873-44-5

Usage

Uses

Used in Pharmaceutical Industry:
4-chloro-N-MethylbenzaMide is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of drugs for treating different medical conditions. Its enzyme-inhibiting properties make it a valuable component in drug discovery and formulation processes.
Used in Chemical Industry:
In the chemical industry, 4-chloro-N-MethylbenzaMide is utilized in the production of various dyes and pigments, playing a significant role in the creation of a wide range of colorants for diverse applications.
Used as an Enzyme Inhibitor:
4-chloro-N-MethylbenzaMide is used as an enzyme inhibitor in the development of drugs, targeting specific enzymes involved in various medical conditions. Its ability to inhibit enzyme activity makes it a useful component in the formulation of therapeutic agents.

InChI:InChI=1/C8H8ClNO/c1-10-8(11)6-2-4-7(9)5-3-6/h2-5H,1H3,(H,10,11)

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 74-89-5 methylamine 
• 82044-38-0 2-methyl-3-p-chlorooxaziridine 
• 134814-86-1 Benzoic acid [(4-chloro-benzoyl)-methyl-amino]-methyl ester 
• 105643-02-5 C₉H₁₀ClNO₃S 
• 106531-24-2 C₁₄H₁₂ClNO₃S 
• 60253-29-4 4-chloro-N-methyl-thiobenzamide 
• 74-11-3 para-chlorobenzoic acid 
• 14062-80-7 N,N-dimethyl-4-chlorobenzamide 
• 26086-60-2 2-azido-4'-chloroacetophenone 
• 104-88-1 4-chlorobenzaldehyde 
• 1144029-00-4 N-methyl-N-tosyloxy-4-chlorobenzamide 
• 19829-08-4 triethylammonium O,O-diisopropyl dithiophosphate 
• 122334-37-6 4-chloro-N-methoxy-N-methylbenzamide 

Downstream Products

• 69746-30-1 5-(4-chlorophenyl)-1-methyl-1H-tetrazole 
• 39083-19-7 p-Chlor-N-methyl-benzimidsaeuremethylester 
• 1026370-84-2 3-(3-bromo-4,5-dimethoxy-phenyl)-5-chloro-3H-isobenzofuran-1-one 
• 158877-61-3 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid [(4-chloro-benzoyl)-methyl-amino]-methyl ester 
• 144175-22-4 N-(diphenyloxophosphinyl)methyl-N-methyl-4-chlorobenzamide 
• 640286-60-8 2-formyl-4-chloro-N-methylbenzamide 
• 1315257-11-4 6-chloro-2-methyl-3,4-diphenylisoquinolin-1(2H)-one 
• 1235478-87-1 6-methoxy-2-methyl-3,4-diphenylisoquinolin-1(2H)-one 
• 97661-68-2 4-chloro-N-methyl-N-nitrosobenzamide 

Relevant academic research and scientific papers

The Pd-catalyzed synthesis of difluoroethyl and difluorovinyl compounds with a chlorodifluoroethyl iodonium salt (CDFI)

Herein, we report a simple and efficient method for the direct installation of chlorodifluoroethyl group onto aromatic molecules of various aromatic amides with a new 2-chloro,2,2-difluoroethyl(mesityl)iodonium salt (CDFI). Moreover, the chlorodifluoroeth

Assemblies of 1,4-Bis(diarylamino)naphthalenes and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water

Host-guest assemblies of a designed 1,4-bis(diarylamino)naphthalene and V-shaped aromatic amphiphiles consisting of two pentamethylbenzene moieties bridged by an m -phenylene unit bearing two hydrophilic side chains emerged as highly reducing photoredox catalysis systems in water. An efficient demethoxylative hydrogen transfer of Weinreb amides has been developed. The present supramolecular strategy permits facile tuning of visible-light photoredox catalysis in water.

Cobalt-catalyzed cyclization of 2-bromobenzamides with carbodiimides: A new route for the synthesis of 3-(imino)isoindolin-1-ones

A novel synthetic pathway to approach 3-(imino)isoindolin-1-ones by the Co-catalyzed cyclization reaction of 2-bromobenzamides with carbodiimides has been developed. This catalytic reaction can tolerate a variety of substituents and provide corresponding products in moderate yields for most cases. According to the literature, the reaction mechanism is proposed through the formation of a five-membered aza-cobalacycle complex, which carries out the following reaction subsequence, including nucleophilic addition and substitution, to furnish the desired structures.

Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones

An efficient enantioselective [3+2] cycloaddition of isomünchnones with methyleneindolinones that are generated by anin situintramolecular addition of the carbonyl group to rhodium carbenes is realized with a chiralN,N′-dioxide/Zn(ii) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values.

Dealkoxylation ofN-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis

Lewis acid-assisted palladium-catalysed dealkoxylation ofN-alkoxyamides has been developed. This reaction proceeded smoothly with a range ofN-alkoxyamides in the absence of an external reductant, thereby establishing a convenient and reductant-free protocol. In addition, a gram-scale reaction could be achieved. Preliminary mechanistic investigations indicated that β-hydrogen elimination from a palladium alkoxide intermediate generated an intramolecular hydride source.

Hydrogen Bond Directed ortho-Selective C?H Borylation of Secondary Aromatic Amides

Reported is an iridium catalyst for ortho-selective C?H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen-bond interactions. The BAIPy-Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho-C?H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C?H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.

Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation

The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.

Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions

Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.

Formation of Aryl [1-Cyano-4-(dialkylamino)butadienyl] Ketones from Pyridines

Treatment of 2-chloropyridine with LDA and the Weinreb amide of benzoic acid afforded three unusual products, namely N -methylbenzamide, 2-chloropyridine-3-methanol, and the ring-opened addition product. This same final product could also be obtained from 2-chloro-3-benzoylpyridine on treatment with LDA. Mechanistic insight for the formation of these products is provided.

Atom-Economical and Tandem Conversion of Nitriles to N-Methylated Amides Using Methanol and Water

A cobalt complex catalyzed tandem conversion of nitrile to N-methylated amide is described using a methanol and water mixture. Using this protocol, several nitriles were directly and efficiently converted to the desired N-methylated amides. Kinetic experiments using H2O18 and CD3OD suggested that water and methanol were the source of the oxygen atom and methyl group, respectively, in the final N-methylated amides. Importantly, the participation of active Co(I)-H species in this transformation was realized from the control experiment. The kinetic isotope effect (KIE) study suggested that the activation of the C-H bond of methanol was a kinetically important step. The Hammett plot confirmed that the reaction was faster with the electron deficient nitriles. In addition, the plausible pathway for the formation of N-methylated amides from the nitriles was supported by the computational study.