112010-43-2

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid, 4-(2-methoxyphenyl)-2,6-dimethyl-, dimethyl ester
• CAS NO: 112010-43-2
• Molecular Formula: C18H19NO5
• Molecular Weight: 329.353
• Mol File: 112010-43-2.mol

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid, 4-(2-methoxyphenyl)-2,6-dimethyl-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid, 4-(2-methoxyphenyl)-2,6-dimethyl-, dimethyl ester(112010-43-2)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid, 4-(2-methoxyphenyl)-2,6-dimethyl-, dimethyl ester(112010-43-2)

Safety Data

• Hazardous Substances Data: 112010-43-2(Hazardous Substances Data)

Upstream product

• 21731-17-9 methyl 3-aminocrotonate 
• 135-02-4 ortho-anisaldehyde 
• 73257-43-9 dimethyl 2,6-dimethyl-4-(2-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate 

Downstream Products

• 97744-29-1 Methyl 2,4-dimethyl-5-oxo-5H-<1>benzopyrano<3,4-c>pyridine-1-carboxylate 

Relevant articles and documents

4-Phenyl-1,2,4-triazole-3,5-dione as a novel and reusable reagent for the aromatization of 1,4-dihydropyridines under mild conditions

4-Substituted 1,3,4-triazole-3,5-diones were used as effective and recyclable oxidizing agents for the oxidation of 1,4-dihydropyridines to the corresponding pyridine derivatives under mild conditions with good to excellent yields.

Superparamagnetic core-shell metal–organic framework Fe3O4@Ni-MOF as efficient catalyst for oxidation of 1,4-dihydropyridines using hydrogen peroxide

A facile and efficient method was described for oxidation of some 3,5-diacyl or 3,5-diester 1,4-dihydropyridines using H2O2 in the presence of superparamagnetic core-shell metal–organic framework Fe3O4@Ni-MOF. The Fe3O4@Ni-MOF has been obtained by Step-by-Step method in which magnetic Fe3O4 magnetic nanoparticles were coated with Ni-MOF using a mercaptoacetic acid linker. The synthesized catalyst was characterized using thermogravimetric analysis, FT-IR spectroscopy, powder X-ray diffraction, field emission scanning electron microscopy and energy-dispersive X-ray analysis. The novel superparamagnetic core-shell metal–organic framework Fe3O4@Ni-MOF revealed high efficiency for oxidation of various 1,4-dihydropyridines using hydrogen peroxide. The Box–Behnken design matrix and the response surface method were applied to investigate the optimization of the reaction conditions. The conditions for optimal reaction yield and time were: amount of catalyst ≈17 mmol, temperature ≈78°C and amount of hydrogen peroxide ≈ 1 ml. A variety of 3,5-diacyl or 3,5-diester 1,4-dihydropyridines with different substituted functional groups have been converted to corresponding pyridines with good to excellent isolated yields using H2O2 and Fe3O4@Ni-MOF. The catalyst was reused up to five times for the oxidation of 1,4-dihydropyridines without a significant loss in catalytic activity. The short reaction times, simplicity of method, good to excellent yields and reusability of catalyst were some advantages of the proposed procedure.

Remarkably fast and selective aromatization of Hantzsch esters with MoOCl4 and MoCl5: A chemical model for possible biologically relevant properties of molybdenum-containing enzymes

Mo(VI) and Mo(V) salts both react selectively with Hantzsch esters to produce substitute pyridines in good-to-excellent yield (75-99%). The remarkable reactivity and selectivity of MoOCl4 under reflux of acetonitrile and MoCl5 in dichloromethane at room temperature encouraged us to propose that molybdenum-containing enzymes (such as xanthine or aldehyde oxidase) also participate to some degree in the metabolism of 1,4-dihydropyridine drugs in the liver analogous to NADH in the respiratory chain.

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.

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.

Synthesis of Dialkyl 2-(2-Hydroxyphenyl)-4,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylates and Alkyl 2,4-Dimethyl-5-oxo-5H-benzopyrano-pyridine-3-carboxylates

The reaction of 2-hydroxybenzaldehydes with 3-oxobutanoic esters and excess ammonia in acetic acid at room temperature yields dialkyl 2-(2-hydroxyphenyl)-4,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylates and their 2-(3,5-dialkoxycarbonyl-4,6-dimethyl-1,2,3-trihydropyridinium-2-yl)-phenoxide zwitterions.Mild oxidation of these compounds is accompanied by lactonisation, with formation of alkyl 2,4-dimethyl-5-oxo-5H-benzopyranopyridine-3-carboxylates, which had previously been incorrectly formulated.Reaction of other o-substituted benzaldehydes with alkyl 3-aminocrotonates in acetic acid at room temperature also yields dialkyl 2-aryl-4,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylates, as well as the normal 1,4-dihydropyridine Hantzsch esters.