14547-81-0

Basic information

• Product Name: 4-methoxy-N-pyridin-2-ylbenzamide
• Synonyms: 4-methoxy-N-pyridin-2-ylbenzamide
• CAS NO: 14547-81-0
• Molecular Formula: C₁₃H₁₂N₂O₂
• Molecular Weight: 228.24658
• Mol File: 14547-81-0.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-methoxy-N-pyridin-2-ylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-N-pyridin-2-ylbenzamide(14547-81-0)
• EPA Substance Registry System: 4-methoxy-N-pyridin-2-ylbenzamide(14547-81-0)

Safety Data

• Hazardous Substances Data: 14547-81-0(Hazardous Substances Data)

Upstream product

• 34813-97-3 2-(formylamino)pyridine 
• 696-62-8 para-iodoanisole 
• 274-87-3 tetrazolo[1,5-a]pyridine 
• 123-11-5 4-methoxy-benzaldehyde 
• 504-29-0 2-aminopyridine 
• 22711-21-3 4-methoxybenzil 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 4160-51-4 1-(4-methoxyphenyl)-1-butanone 
• 121-97-1 4-Methoxypropiophenone 
• 104-01-8 4-Methoxyphenylacetic acid 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 768-60-5 4-methoxyphenylacetylen 
• 31562-99-9 2-(4-methoxyphenyl)imidazo[1,2-a]pyridine 
• 100-09-4 4-methoxybenzoic acid 

Downstream Products

• 86843-96-1 2-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine 

Relevant articles and documents

N-pyridinylbenzamides: an isosteric approach towards new antimycobacterial compounds

A series of N-pyridinylbenzamides was designed and prepared to investigate the influence of isosterism and positional isomerism on antimycobacterial activity. Comparison to previously published isosteric N-pyrazinylbenzamides was made as an attempt to draw structure–activity relationships in such type of compounds. In total, we prepared 44 different compounds, out of which fourteen had minimum inhibitory concentration (MIC) values against Mycobacterium tuberculosis H37Ra below 31.25?μg/ml, most promising being N-(5-chloropyridin-2-yl)-3-(trifluoromethyl)benzamide (23) and N-(6-chloropyridin-2-yl)-3-(trifluoromethyl)benzamide (24) with MIC?=?7.81?μg/ml (26?μm). Five compounds showed broad-spectrum antimycobacterial activity against M. tuberculosis H37Ra, M. smegmatis and M. aurum. N-(pyridin-2-yl)benzamides were generally more active than N-(pyridin-3-yl)benzamides, indicating that N-1 in the parental structure of N-pyrazinylbenzamides might be more important for antimycobacterial activity than N-4. Marginal antibacterial and antifungal activity was observed for title compounds. The hepatotoxicity of title compounds was assessed in vitro on hepatocellular carcinoma cell line HepG2, and they may be considered non-toxic (22 compounds with IC50 over 200?μm).

Exploring Homogeneous Conditions for Mild Buchwald-Hartwig Amination in Batch and Flow

Cross-couplings are among the most frequently used reactions in complex molecule synthesis. However, the requirement of stoichiometric base can cause challenges. Harsh, insoluble inorganic bases can lead to poor tolerance of sensitive functional groups, scale-up issues, and difficult adaptation to continuous flow platforms. Herein, we describe the use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g., XantPhos) with DBU as a soluble, functional-group-tolerant, homogeneous base. Application of this system to diverse aminations in batch and flow are demonstrated, as is the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions.

Direct Transformation of Alkylarenes into N-(Pyridine-2-yl)amides by C(sp3)–C(sp3) Bond Cleavage

C(sp3)–H bond functionalization and C(sp3)–C(sp3) bond cleavage are very challenging transformations in chemistry. Herein, we report a mild and green methodology for the construction of N-(pyridine-2-yl)amides via tandem C(sp3)–H activation/C–C bond cleavage of alkylarenes. Various N-heterocyclic amides were directly synthesized from alkylarenes in water in moderate to good yields.