54979-78-1

Basic information

• Product Name: 2-chloro-N-(pyridin-2-yl)benzamide
• Synonyms: benzamide, 2-chloro-N-2-pyridinyl-
• CAS NO: 54979-78-1
• Molecular Formula: C₁₂H₉ClN₂O
• Molecular Weight: 232.6657
• Mol File: 54979-78-1.mol

Chemical Properties

• Boiling Point: 307.3°C at 760 mmHg
• Flash Point: 139.6°C
• Density: 1.341g/cm³
• Vapor Pressure: 0.000732mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 2-chloro-N-(pyridin-2-yl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-N-(pyridin-2-yl)benzamide(54979-78-1)
• EPA Substance Registry System: 2-chloro-N-(pyridin-2-yl)benzamide(54979-78-1)

Safety Data

• Hazardous Substances Data: 54979-78-1(Hazardous Substances Data)

Upstream product

• 504-29-0 2-aminopyridine 
• 609-65-4 o-chlorobenzoyl chloride 
• 89-98-5 2-chloro-benzaldehyde 
• 21854-95-5 2,2'-dichlorobenzil 
• 1152034-94-0 2-(2-chlorophenyl)-N-cyclohexylimidazolo[1,2-a]pyridin-3-amine 
• 853706-94-2 N-(tert-butyl)-2-(2-chlorophenyl)imidazo[1,2-a]pyridin-3-amine 
• 5029-67-4 2-iodopyridine 
• 609-66-5 2-chlorobenzamide 

Downstream Products

• 53439-81-9 benzo[c][1,8]naphthyridin-6(5H)-one 
• 185540-17-4 (4-aminopyridin-3-yl)(2-chlorophenyl)methanone 

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).

Diverse Oxidative C(sp2)-N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides

An efficient and chemoselective C(sp2)-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some α-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.

Copper Catalyzed Oxidative C-C Bond Cleavage of 1,2-Diketones: A Divergent Approach to 1,8-Naphthalimides, Biphenyl-2,2′-dicarboxamides, and N-Heterocyclic Amides

We report here a simple and efficient copper catalyzed oxidative C-C bond cleavage of stable aromatic cyclic-fused and acyclic 1,2-diketones to deliver amides and imides in high yields. This newly developed protocol provides an excellent tool to transform structurally different 1,2-diketones into different products under the same reaction conditions. The key synthetic features of this methodology are the formation of 1,8-naphthalimides and biphenyl-2,2′-dicarboxamide motifs in high yields. The fluorescent studies of 1,8-naphthalimide derivatives were also carried out in order to show the potential application of these scaffolds.

Potassium Carbonate Promoted C-N Coupling Reaction between Benzamides and Aryl Iodides

A practical and efficient method for N-arylation of benz-amides promoted by potassium carbonate in the presence of DMEDA was developed. The reaction was carried out without addition of any transition-metal catalyst to afford a variety of N-arylated products in moderate to good yields (up to 97%).

Synthesis method of N-heterocyclic acylamide derivative

The invention discloses a synthesis method of an N-heterocyclic acylamide derivative. A reaction general formula is as shown in the specification. According to the synthesis method, an imidazo heterocyclic amine compound I is taken as a raw material; unde

Transformation of aldehydes or alcohols to amides at room temperature under aqueous conditions

A novel and efficient method for the synthesis of amide has been developed. The reactions proceeded smoothly under aqueous conditions at room temperature and generated the corresponding products in good to excellent yields. It is worth noting that alkyl amines which did not react in known approaches are well tolerated in our system.

Metal-free oxidative amidation of aldehydes with aminopyridines employing aqueous hydrogen peroxide

The first metal free report on the amidation of aldehydes with aminopyridines was accomplished using simple aqueous hydrogen peroxide (aq. H2O2) as the oxidant. No catalysts or additives were needed for this transformation and the reaction proceeded in water, an environmentally benign reaction medium. Green oxidant and reaction conditions, and the ability to construct diverse N-(pyridin-2-yl)benzamide by this elegant method render it a practical alternative for the synthesis of these amides.

Copper-catalyzed highly efficient oxidative amidation of aldehydes with 2-aminopyridines in an aqueous micellar system

An environmentally benign protocol for the synthesis of N-(pyridine-2-yl)amides from aldehydes and 2-aminopyridines has been developed under mild reaction conditions. This approach requires Cu(OTf)2 as a catalyst, and inexpensive molecular iodi

Pyridyl benzamides as a novel class of potent inhibitors for the kinetoplastid Trypanosoma brucei

A whole-organism screen of approximately 87000 compounds against Trypanosoma brucei brucei identified a number of promising compounds for medicinal chemistry optimization. One of these classes of compounds we termed the pyridyl benzamides. While the initial hit had an IC50 of 12 μM, it was small enough to be attractive for further optimization, and we utilized three parallel approaches to develop the structure-activity relationships. We determined that the physicochemical properties for this class are generally favorable with particular positions identified that appear to block metabolism when substituted and others that modulate solubility. Our most active compound is 79, which has an IC50 of 0.045 μM against the human pathogenic strain Trypanosoma brucei rhodesiense and is more than 4000 times less active against the mammalian L6 cell line.

Copper-catalyzed dehydrogenative reaction: Synthesis of amide from aldehydes and aminopyridine

We have developed a highly efficient method in the presence of copper catalyst to form amides from aminopyridines and aldehydes. This method is simple, environmental benign and has practical advantages in the amide synthesis.