24056-08-4

Basic information

• Product Name: Benzamide, N,4-dimethoxy-
• CAS NO: 24056-08-4
• Molecular Formula: C9H11NO3
• Molecular Weight: 181.191
• Mol File: 24056-08-4.mol

Chemical Properties

• CAS DataBase Reference: Benzamide, N,4-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N,4-dimethoxy-(24056-08-4)
• EPA Substance Registry System: Benzamide, N,4-dimethoxy-(24056-08-4)

Safety Data

• Hazardous Substances Data: 24056-08-4(Hazardous Substances Data)

Upstream product

• 57139-36-3 (Z)-4-methoxy-O-methylbenzohydroximoyl chloride 
• 67-62-9 O-Methylhydroxylamin 
• 100-07-2 4-methoxy-benzoyl chloride 
• 593-56-6 N-methoxylamine hydrochloride 
• 4229-44-1 N-methylhydroxyamine hydrochloride 
• 155164-68-4 4,5-Dichloro-2-(4-methoxy-benzoyl)-2H-pyridazin-3-one 
• 100-09-4 4-methoxybenzoic acid 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 63697-31-4 Trimethyl-p-methoxybenzoylhydrazonium-Iodid 
• 57139-22-7 potassium p-methoxylbenzohydroxamate 
• 74-88-4 methyl iodide 
• 108-67-8 1,3,5-trimethyl-benzene 

Downstream Products

• 38192-16-4 bis-(4-methoxy-benzoyl)-diazene 
• 137042-63-8 C₉H₁₀ClNO₂ 
• 137042-67-2 3-bromo-4-methoxybenzonitrile 
• 1202932-77-1 N,2,4-trimethoxybenzamide 
• 1312588-28-5 N-(3,5-dimethylbenzyl)-N-methoxy-4-methoxybenzamide 
• 121-98-2 methyl 4-methoxybenzoate 
• 1225462-91-8 6-methoxy-2,3-diphenylisoquinolin-1(2H)-one 
• 1360651-30-4 6-(trifluoromethyl)-3,4-diphenylisoquinolin-1(2H)-one 
• 1417712-57-2 (R)-2-(1-cyclohexylidene-4-methoxybutan-2-yl)-N,4-dimethoxybenzamide 
• 1440755-89-4 C₁₇H₁₆O₃ 
• 1440755-93-0 (E)-N,4-dimethoxy-2-(4-methylstyryl)benzamide 
• 1440754-69-7 (E)-tert-butyl (5-methoxy-2-(methoxycarbamoyl)-3-(4-methylstyryl)phenyl)carbamate 
• 1440755-83-8 C₁₇H₁₇NO₂ 
• 1456693-90-5 3-hydroxy-2,5-dimethoxy-3-phenylisoindolin-1-one 

Relevant articles and documents

Pd(II)-catalyzed annulation reactions of epoxides with benzamides to synthesize isoquinolones

Epoxides as alkylating reagents are unprecedentedly applied in Pd(II)-catalyzed C?H alkylation and oxidative annulation of substituted benzamides to synthesize isoquinolones rather than isochromans, which is accomplished through alerting the previously reported reaction mechanism by the addition of oxidant and TEA. Under these conditions, various isoquinolones have been prepared with yields up to 92%. In addition, this methodology has been successfully employed in the total syntheses of rupreschstyril, siamine, and cassiarin A in an expedient fashion.

Pd/C-catalyzed aerobic oxidative C–H alkenylation of arenes in γ-valerolactone (GVL)

A novel methodology for the heterogeneous palladium-catalyzed C–H alkenylation of N-methoxybenzamides and anilides is presented. This approach is based on the use of commercially available Pd/C as catalyst and molecular oxygen as terminal oxidant, in comb

Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of: N -methoxybenzamides with a Rh(iii)-catalyst

Hypervalent iodonium ylides expeditiously generate carbenes which undergo domino intermolecular C-H activation followed by intramolecular condensation in the presence of N-methoxybenzamide as a starting material and a Rh(iii)-catalyst to afford dihydrophenanthridines. KIE studies and DFT calculations were performed to substantiate the mechanistic pathway. To extend the synthetic utilisation, fluorescent pyranoisocoumarins were achieved by using Rh(iii)-catalyzed peri-C-H/O-H activation/annulation reactions.

Palladium-Catalyzed Inert C?H Bond Activation and Cyclocarbonylation of Isoquinolones with Carbon Dioxide Leading to Isoindolo[2,1-b]isoquinoline-5,7-Diones

A palladium-catalyzed inert C?H bond activation and cyclocarbonylation of isoquinolones leading to isoindolo[2,1-b]isoquinoline-5,7-diones under 1 atm of carbon dioxide has been developed. This transformation features high regio- and chemo-selectivity, step-economy, and good functional group tolerance. Most of the corresponding products were obtained in moderate to good yields. It offers an alternative approach for the synthesis of useful diverse isoindolo[2,1-b]isoquinoline-5,7-dione derivatives. (Figure presented.).

Rhodium(III)-catalyzed chemodivergent annulations between: N-methoxybenzamides and sulfoxonium ylides via C-H activation

Chemodivergent and redox-neutral annulations between N-methoxybenzamides and sulfoxonium ylides have been realized via Rh(iii)-catalyzed C-H activation. The sulfoxonium ylide acts as a carbene precursor, and coupling occurs under acid-controlled condition

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 °C and were applied in the C?H arylation of unactivated arenes using either rhodium or ruthenium catalysts. A broad range of heterocyclic systems of high interest for synthetic and medicinal chemistry was accessed in high yields. The developed C?H functionalization could not be achieved using reported reagents or methods, highlighting the unique reactivity of Indole- and Pyrrole-BX.

Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones

A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.).

C-F bond cleavage enabled redox-neutral [4+1] annulation via C-H bond activation

Using α,α-difluoromethylene alkyne as a nontraditional one-carbon reaction partner, a synthetically novel method for the construction of isoindolin-1-one derivatives via Rh(III)-catalyzed [4+1] annulation reaction is reported. The 2-fold C-F bond cleavage not only enables the generation of desired product under an overall oxidant-free condition but also results in a net migration of carbon-carbon triple bond. In addition, the present reaction protocol exhibits a tolerance of a wide spectrum of functional groups due to the mild reaction conditions employed.

Selective mono-alkylation of N-methoxybenzamides

We report our latest discovery of norbornene derivative modulated highly mono-selective ortho-C-H activation alkylation reactions on arenes bearing simple mono-dentate coordinating groups. The reaction features the use of readily available benzamides and alkyl halides. During the study, we prepared 30 mono-alkylated aryl amides in good yields with good mono-selectivity. We have also demonstrated that structurally rigid alkenes such as norbornene and its derivatives are a good class of ligand and could be used for future direct C-H functionalizations. The utilization of norbornene type ligands for assistance in C-H activation processes has opened a new window for future molecular design using direct C-H functionalization strategies.

Ir(III)-Catalyzed Carbenoid Functionalization of Benzamides: Synthesis of N-Methoxyisoquinolinediones and N-Methoxyisoquinolinones

A mild and efficient Ir(III)-catalyzed C-H carbenoid functionalization strategy has been developed to access N-methoxyisoquinolinediones and N-methoxyisoquinolinones. The reaction proceeds efficiently in high yield at room temperature over a broad range of substrates without requirement of any additional oxidants or a base.