15547-66-7

Basic information

• Product Name: N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide
• Synonyms: N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide
• CAS NO: 15547-66-7
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.36364
• Mol File: 15547-66-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 127-129 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: 505.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.130±0.06 g/cm3(Predicted)
• PKA: 14.68±0.46(Predicted)
• CAS DataBase Reference: N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide(15547-66-7)
• EPA Substance Registry System: N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxybenzamide(15547-66-7)

Safety Data

• Hazardous Substances Data: 15547-66-7(Hazardous Substances Data)

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 696-63-9 4-Methoxybenzenethiol 
• 201230-82-2 carbon monoxide 
• 1541168-57-3 N-[2-(3,4-dihydroxyphenyl)ethyl]-4-methoxybenzamide 
• 74-88-4 methyl iodide 
• 3424-93-9 4-methoxyphenylacetamide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 4230-93-7 3,4-dimethoxynitrostyrene 

Downstream Products

• 15547-67-8 6,7-dimethoxy-1-(4-methoxy-phenyl)-isoquinoline 
• 70319-15-2 (±)-6,7-dimethoxy-1-(4-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1448701-61-8 (+)-6,7-dimethoxy-1-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 15462-83-6 6,7-dimethoxy-1-<(para-methoxy)phenyl>-3,4-dihydroisoquinoline 

Relevant articles and documents

Cobalt catalysed aminocarbonylation of thiols in batch and flow for the preparation of amides

The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the formation of disulfides and ureas can be limited. The process works well with aromatic thiols with electron donating groups (EDG) whereas other thiols give reaction with lower yields. The previous process has been transferred and optimized into flow equipment, thus allowing using less CO in a safer way, and permitting the scaling up of the synthesis. Two drugs, moclobemide and itopride were prepared with this methodology, albeit only in the second case with good results. A mechanistic pathway is proposed.

Josiphos-Type Binaphane Ligands for Iridium-Catalyzed Enantioselective Hydrogenation of 1-Aryl-Substituted Dihydroisoquinolines

Convenient synthesis and useful application of a series of Josiphos-type binaphane ligands were described. The iridium complexes of these chiral diphosphines displayed excellent enantioselectivity and good reactivity in the asymmetric hydrogenation of challenging 1-aryl-substituted dihydroisoquinoline substrates (full conversions, up to >99% ee, 4000 TON). The use of 40% HBr (aqueous solution) as an additive dramatically improved the asymmetric induction of these catalysts. This transformation provided a highly efficient and enantioselective access to chiral 1-aryl-substituted tetrahydroisoquinolines, which were of great importance and common in natural products and biologically active molecules.

Rhodium catalyzed cyanation of chelation assisted C-H bonds

A rhodium-catalyzed cyanation of chelation assisted C-H bonds is described employing N-cyano-N-phenyl-p-methylbenzenesulfonamide as an efficient cyanating reagent. The present method allowed the synthesis of various benzonitirle derivatives in good to excellent yield. A number of chelating groups are also effective in the present cyanation of C-H bonds. In addition, the developed methodology was applied in the formal synthesis of the isoquinoline alkaloid, menisporphine.