24303-02-4

Upstream product

• 59-67-6 nicotinic acid 
• 106-49-0 p-toluidine 
• 103-89-9 4-Methylacetanilide 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 4013-72-3 nicotinoyl azide 
• 99-99-0 1-methyl-4-nitrobenzene 
• 98-92-0 nicotinamide 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 624-31-7 4-tolyl iodide 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 

Downstream Products

• 5454-86-4 NSC 23247 
• 5768-40-1 4-(nicotinamido)benzoic acid 
• 1329664-01-8 C₂₇H₂₀N₂O 
• 1329664-03-0 C₂₇H₂₀N₂O 
• 1607469-45-3 fac-[Re(CO)₃(2,2′-bipyridine)(N-(p-tolyl)nicotinamide)][OTf] 

Relevant academic research and scientific papers

Switching from biaryl formation to amidation with convoluted polymeric nickel catalysis

A stable, reusable, and insoluble poly(4-vinyl-pyridine) nickel catalyst (P4VP-NiCl2) was prepared through the molecular convolution of poly(4-vinylpyridine) (P4VP) and nickel chloride. We proposed a coordination structure of the Ni center in the precatalyst based on elemental analysis and Ni K-edge XANES, and we confirmed that it is consistent with Ni K-edge EXAFS. The Suzuki?Miyaura-type coupling of aryl halides and arylboronic esters proceeded using P4VP-NiCl2 (0.1 mol % Ni) to give the corresponding biaryl compounds in up to 94% yield. Surprisingly, when the same reaction of aryl halides and arylboronic acid/ester was carried out in the presence of amides, the amidation proceeded predominantly to give the corresponding arylamides in up to 99% yield. In contrast, the reaction of aryl halides and amides in the absence of arylboronic acid/ester did not proceed. P4VP-NiCl2 successfully catalyzed the lactamization for preparing phenanthridinone. P4VP-NiCl2 was reused five times without significant loss of catalytic activity. Pharmaceuticals, natural products, and biologically active compounds were synthesized efficiently using P4VPNiCl2 catalysis. Nickel contamination in the prepared pharmaceutical compounds was not detected by ICP-MS analysis. The reaction was scaled to multigrams without any loss of chemical yield. Mechanistic studies for both Suzuki?Miyaura and amidation were performed.

Efficient conversion of acids and esters to amides and transamidation of primary amides using OSU-6

OSU-6, an MCM-41 type hexagonal mesoporous silica with strong Bronsted acid properties, has been used to promote the high-yield conversion of carboxylic acids and esters to carboxamides as well as transamidations of primary amides in a one-pot solventless approach. A metal-free heterogeneous catalyst that promotes all of these processes has not been previously reported. OSU-6 enables these transformations to proceed in shorter times and at lower temperatures for a broad range of substrates. An added benefit is that the catalyst can be recycled and reused multiple times without significant loss of activity.

An organometallic complex revealing an unexpected, reversible, temperature induced SC-SC transformation

A reversible, temperature driven phase transformation that takes place at ca. 180 K, in a single-crystal to single-crystal manner, has been observed for a monometallic transition metal coordination complex based on a fac-Re(CO) 3 core, with a c

Microwave-assisted heteropolyanion-based ionic liquids catalyzed transamidation of non-activated carboxamides with amines under solvent-free conditions

An environmentally benign and highly efficient protocol for the transamidation of non-activated carboxamides with amines using heteropolyanion-based ionic liquids as catalysts under microwave-assisted and solvent-free conditions has been developed. As evaluated by the reactions of a structurally diverse set of amides and amines, the scope and utility of the transamidation proved to be quite general. Operational simplicity, solvent-free media, the potential reusability of catalysts and wide functional group tolerance are attractive features. This method provides a much improved protocol over the existing methods.

Benzoic acid-catalyzed transamidation reactions of carboxamides, phthalimide, ureas and thioamide with amines

An efficient and simple method for the transamidation of carboxamides, phthalimide, ureas and thioamide with amines catalyzed by commercially available benzoic acid under metal-free conditions is described. Furthermore, to the best of our knowledge, this is the first report about the transamidation of an aromatic thioamide with amines.

Structural systematics and conformational analyses of a 3 × 3 isomer grid of nine N-(tolyl)pyridinecarboxamides and three chlorinated relatives

A 3 × 3 isomer grid of nine N-(tolyl)pyridinecarboxamides (NxxM, x = para-/meta-/ortho-) integrating crystal structure analyses, ab initio calculations (gas phase and PCM-SMD solvated in CH2Cl2, H2O) and conformational stu

N-arylamides from selenium-catalyzed reactions of nitroaromatics and amides in the presence of carbon monoxide and mixed organic bases

N-Arylamides were exclusively obtained in moderate to good yields from selenium-catalyzed reactions of nitroaromatics with amides in the presence of CO and mixed organic bases Et3N and DBU.

AN UNUSUAL SYNTHESIS OF NICOTINAMIDES

Reaction of 2,3-pyridinedicarboxylic anhydride (1) with a substituted aniline (2) in acetic acid gave rise to a mixture of two products.These two products were identified as the cyclic imide (4) and nicotinamide (5).A mechanistic scheme consistent with empirical observations is proposed.

POLAROGRAPHIC REDUCTION OF 1-BENZYL-N-(p-X-PHENYL)-3-AMINOCARBONYLPYRIDINIUM SALTS

The substitution effect of different groups X (N(CH2CH3)2, OH, OCH3, CH3, NHCOCH3, H, Cl, COOCH2CH3 and NO2) on the polarographic behaviour of 3-(N-p-X-phenylaminocarbonyl)pyridines (I),1-benzyl-N-(p-X-phenyl)-3-aminocarbonylpyridinium cations (II) and their respective 1,4-dihydroderivatives (III) has been investigated in anhydrous solution of dimethylformamide with 0.1 mol 1-1 (n-C4H9)4N+PF6- as supporting electrolyte.The half-wave potentials of the reduction wave of I and II, which correspond to the uptake of a single electron (wave B) and to the formation of a primary radical, obey a Hammett correlation in a similar way as it is in the case of 1-benzyl- and 1-phenyl-3-amino-carbonylopyridinium cations substituted at carbon 4 on the benzene nucleus.The slope q?,R in the Hammett plot equals 0.192 V (I) and 0.104 V (II) for anhydrous DMF and compares thus with this slope obtained with the 1-benzyl- and 1-phenyl derivatives in our previous communications.

Heteroacyl Azides as Acylating Agents for Aromatic or Heteroatomic Amines (1)

The possibility of formation of substituted heterocyclic amides from heteroacyl azides and aromatic or heteroatomic amines was investigated.Although acylation proceeded in some cases under mild reaction conditions, formation of N,N'-disubstituted ureas was the main process at elevated temperatures.