103026-82-0

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid, 4-(3-chlorophenyl)-2,6-dimethyl-, dimethyl ester
• CAS NO: 103026-82-0
• Molecular Formula: C17H16ClNO4
• Molecular Weight: 333.771
• Mol File: 103026-82-0.mol

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid, 4-(3-chlorophenyl)-2,6-dimethyl-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid, 4-(3-chlorophenyl)-2,6-dimethyl-, dimethyl ester(103026-82-0)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid, 4-(3-chlorophenyl)-2,6-dimethyl-, dimethyl ester(103026-82-0)

Safety Data

• Hazardous Substances Data: 103026-82-0(Hazardous Substances Data)

Upstream product

• 73257-45-1 1,4-dihydro-2,6-dimethyl-4-(3-chlorophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester 
• 136814-25-0 dimethyl 7-(3-chlorophenyl)-5,8a-dimethyl-2,3,7,8-tetrahydro-7H-oxazolo<3,2-a>pyridin-6,8-dicarboxylate 

Downstream Products

• 1015135-68-8 dimethyl 6-(3-chlorophenyl)-3,4-dimethyl-2,5-pyridinedicarboxylate 
• 1015135-67-7 dimethyl 2-(3-chlorophenyl)-5,6-dimethyl-3,4-pyridinedicarboxylate 

Relevant articles and documents

Enantiospecific synthesis of dihydropyridines from chiral enamines

A new asymmetric synthesis of dihydropyridines is described. This methodology is based on the use of chiral aminoalcohols to produce enamines, which were used in the synthesis of enantiopure 2-alkyl-2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridines. The known stereochemistry of these compounds was exploited to obtain 1,4-dihydropyridines with controlled configuration at C-4.

Photochemistry of Hantzsch 1,4-dihydropyridines and pyridines

The photochemistry of some Hantzsch 4-phenyl-1,4-dihydropyridines bearing a substituent on the phenyl ring (the three isomeric chloro derivatives and the 4′-nitro derivative) has been studied. All of these compounds underwent inefficient aromatization to

An efficient, metal-free, room temperature aromatization of Hantzsch-1,4-dihydropyridines with urea-hydrogen peroxide adduct, catalyzed by molecular iodine

A mild, highly efficient and metal-free synthetic method for aromatization of 1,4-dihydropyridines employing urea-hydrogen peroxide adduct as oxidant catalyzed by 20 mol % of molecular iodine was developed. The reaction was carried out in ethyl acetate at room temperature and the products were isolated in high to excellent yields. A plausible free-radical mechanism is proposed based on results obtained with derivatives having alkyl and aryl substituents in the 1,4-dihydropyridine ring.

A highly efficient biomimetic aromatization of Hantzsch-1,4-dihydropyridines with t-butylhydroperoxide, catalysed by iron(III) phthalocyanine chloride

Rapid aromatization of Hantzsch-1,4-DHPs with t-butylhydroperoxide catalysed by iron(III) phthalocyanine chloride is described. The reaction proceeds smoothly at room temperature within 1-35 min and the products of high purity were isolated in excellent yields. To explain the reactivity of this catalytical system plausible mechanism have been proposed to involve formation of high-valent oxoferryl species as in cytochrome P450 itself.

Rapid, efficient, room temperature aromatization of Hantzsch-1,4-dihydropyridines with vanadium(V) salts: superiority of classical technique versus microwave promoted reaction

The aromatization of 1,4-dihydropyridines (1,4-DHPs) employing group 4 (Zr and Hf) and 5 (V, Nb, Ta) elements of periodic system has been studied. The reaction with VOCl3 in dichloromethane at room temperature afforded products, substituted pyridines, in high-to-excellent yield. For the first time, the formation of charge-transfer complexes (CTCs) has been evidenced in preorganization step between 1,4-DHP and oxidant before electron transfer. The CTC has been formed only in neutral solvents such as dichloromethane and is characterized by intensive coloration. The aromatization of 1,4-DHP with V2O5 in refluxing acetic acid has found to be superior over microwave promoted reaction in solventless media. The only reasonable explanation was found in polymeric structure of V2O5, which slowly transfer energy of microwaves needed for the activation of the reactants. The solvent polarity dependent oxidative dealkylation of 4-n-propyl-1,4-DHP has been discovered. Unexpectedly, the reaction in acetic acid afforded only 33% of dealkylated product compared to 91% obtained in dichloromethane under the same reaction conditions.

Mild, selective, and high-yield oxidation of hantzsch 1,4-dihydropyridines with lead(IV) acetate

Aromatization of 1,4-dihydropyridines with lead(IV) acetate under mild reaction conditions is described. The method is very selective, mild and versatile in the synthesis of different substituted pyridines.

Oxidation of dihydropyridine calcium channel blockers and analogues by human liver cytochrome P-450 IIIA4

A series of 21 different 4-substituted 2,6-dimethyl-3-(alkoxycarbonyl)-1,4-dihydropyridines was considered with regard to oxidation to pyridine derivatives by human liver microsomal cytochrome P-450 (P-450). Antibodies raised against P-450 IIIA4 inhibited the microsomal oxidation of nifedipine and felodipine to the same extent, as did cimetidine and the mechanism-based inactivator gestodene. Gestodene was ~ 103 times more effective an inhibitor than cimetidine, on a molar basis. When rates of oxidation of the 1,4-dihydropyridines were compared to each other in different human liver microsomal preparations, all were highly correlated with each other with the exceptions of a derivative devoid of a substituent at the 4-position and an N1-CH3 derivative. A P-450 IIIA4 cDNA clone was expressed in yeast and the partially purified protein was used in reconstituted systems containing NADPH-cytochrome P-450 reductase and cytochrome b5. This system catalyzed the oxidation of all of the 1,4-dihydropyridines except the two for which poor correlation was seen in the liver microsomes. Principal component analysis supported the view that most of these reactions were catalyzed by the same enzyme in the yeast P-450 IIIA4 preparation and in the different human liver microsomal preparations, or by a closely related enzyme showing nearly identical properties of catalytic specificity and regulation. The results indicate that the enzyme P-450 IIIA4 is probably the major human catalyst involved in the formal dehydrogenation of most but not all 1,4-dihydropyridine drugs.