39562-16-8

Basic information

• Product Name: ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE
• Synonyms: ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE;3-NITROBENZYLIDENEETHYLESTER;Butanoic acid, 2-[(3-nitrophenyl)methylene]-3-oxo, ethyl ester;Ethyl -aceto-(m-nitrobenzylidene)acetate;ETHYL (E)-2-(3-NITROBENZYLIDENE)-3-OXOBUTANOATE;Ethyl 3-nitrobenzylideneacetoacetate;Ethyl alpha-acetyl-beta-(m-nitrophenyl)acrylate;NSC 637307
• CAS NO: 39562-16-8
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.27
• EINECS: 404-490-0
• Mol File: 39562-16-8.mol

Chemical Properties

• Melting Point: 160℃ (ethanol )
• Boiling Point: 399.2°C at 760 mmHg
• Flash Point: 171.3°C
• Appearance: /
• Density: 1.261g/cm³
• Vapor Pressure: 1.4E-06mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE(39562-16-8)
• EPA Substance Registry System: ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE(39562-16-8)

Safety Data

• Hazard Codes: Xi
• Statements: 41-43-52/53
• Safety Statements: 24-26-37/39-61
• Hazardous Substances Data: 39562-16-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE is used as an intermediate in the synthesis of 5-Ethyl-demethyl Lercanidipine (E913200), which is an impurity of Lercanidipine (L179000). Lercanidipine is a dihydropyridine calcium channel blocker that is commonly used in the treatment of hypertension and angina pectoris. The synthesis of ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE allows for the production of a more effective and safer medication for patients suffering from these cardiovascular conditions.
Used in Quality Control and Impurity Profiling:
In the pharmaceutical industry, ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE is also used for quality control and impurity profiling of Lercanidipine. By understanding the presence and characteristics of ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE, researchers and manufacturers can ensure the purity and efficacy of the final drug product, ultimately contributing to the safety and well-being of patients who rely on these medications.
Used in Research and Development:
As a key intermediate in the synthesis of specific pharmaceutical compounds, ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE is also utilized in research and development efforts within the pharmaceutical sector. Scientists and researchers use ETHYL 2-ACETYL-3-(3-NITROPHENYL)PROPENOATE to explore new methods of synthesis, investigate potential applications, and develop innovative treatments for various medical conditions.

InChI:InChI=1/C13H13NO5/c1-3-19-13(16)12(9(2)15)8-10-5-4-6-11(7-10)14(17)18/h4-8H,3H2,1-2H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 99-61-6 3-nitro-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 110-89-4 piperidine 

Downstream Products

• 17064-93-6 N-(3-nitrobenzylidene)-O-toluidine 
• 98050-72-7 5-(ethoxycarbonyl)-2,6-dimethyl-4-(m-nitrophenyl)-1,4(3,4)-dihydropyrimidine 
• 143996-69-4 6-Methyl-4-(3-nitro-phenyl)-2-phenyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 79823-50-0 2,3,4,5,6,9-Hexahydro-1,4,8-trimethyl-6-(3-nitrophenyl)-5-oxo-1H-pyrido<2,3-e><1,4>diazepin-7-carbonsaeure-ethylester 
• 86781-08-0 cyclopropylmethyl ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 103772-87-8 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cyclobutylmethyl ester 5-ethyl ester 
• 86780-93-0 Ethyl 2,2-ethylenedioxypropyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 86780-92-9 Ethyl 3,3-ethylenedioxybutyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 75130-25-5 3-(2-cyanoethyl) 5-ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 39562-23-7 2,6-dimethyl-4-(3'-nitrophenyl)1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-allyl ester 
• 92406-55-8 3-Cyclopentyl-1,6-dimethyl-4-(3-nitro-phenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester; hydrochloride 
• 88284-24-6 octyl 2,6-dimethyl-3-carbethoxy-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate 
• 113568-03-9 C₃₆H₃₈N₄O₁₂ 
• 113568-04-0 C₃₈H₄₂N₄O₁₂ 

Relevant articles and documents

Novel halogenated 1,4-dihydropyridines: synthesis, bioassay, microsomal oxidation and structure-activity relationships

Nine new 1,4-dihydropyridines (DHPs) were synthesized and evaluated for their relaxant ability (rat aorta) and their antihypertensive activity in spontaneously hypertensive rats; their microsomal oxidation rate (MOR) was determined.In terms of relaxant activity, the 4-(3,5-difluorophenyl) analogues were more potent than those with 4-(4-fluorophenyl) but weaker than those with 4-(3-nitrophenyl) substituents, while in terms of antihypertensive activity the 4-(3,5-difluorophenyl) derivatives were more potent than their 4-(3-nitrophenyl) analogues.Their MOR could beexplained the basis of the electron-withdrawing effect of the substituents, and in some cases they permitted a rationalization of discrepancies noted between DHP antihypertensive and relaxant activities.A parabolic relationship was found between the size of the carboxylic ester substituents and their contributions calculated from a Free-Wilson/Fujita-Ban analysis of relaxant activity data. 1,4-dihydropyridine / aorta relaxant activity / antihypertensive activity / microsomal oxidation rate / structure-activity relationship.

Based on the three-step synthesis process of preparation of the nitrendipine (by machine translation)

The invention discloses a method based on three-step preparation of the nitrendipine synthesis process, comprising the following steps: S1 ammoniation reaction: liquid ammonia with methyl acetoacetate reflect the generated β - amino-crotonic acid methyl ester; S2 condensation reaction: will be m formaldehyde and acetyl ethyl acetate in the catalyst piperidine and glacial acetic acid under the action of the condensation reaction to obtain the pure 2 - (3 - nitryl asia phenmethyl) - acetyl ethyl acetate; S3 ring-closure reaction: the β - amino-crotonic acid methyl ester with 2 - (3 - nitryl asia phenmethyl) - acetyl ethyl acetate in the catalyst diisopropyl ethylamine/glacial acetic acid under the action of the Michael reaction, then molecule in cyclization to obtain nitrendipine; S4 refining, the invention - nitrobenzaldehyde between (SM1), acetyl ethyl acetate (SM2) and methyl acetoacetate (SM3) as the starting raw material preparation, heating the ring, three-step reaction qualified products can be obtained nitrendipine, not containing special reaction conditions. (by machine translation)

Design and synthesis of 4-alkyl-2-amino(acetamino)-6-aryl-1,3-thiazine derivatives as influenza neuraminidase inhibitors

With a convenient and economical method, two series of 1,3-thiazine derivatives 1 and 2 were synthesized, and their neuraminidase (NA) inhibitory activities were evaluated. The pharmacological results showed that most of the compounds have potent NA inhibitory activity. Especially, 1g exhibited the best activity against influenza virus A (H1N1) NA (IC50 = 29.06 μg/mL), and its crystal structure was determined by single-crystal X-ray diffraction. The preliminary biological assay indicated that 1,3-thiazine could be used as a core structure to design novel influenza NA inhibitors. Two series of novel 1,3-thiazine analogs were synthesized and their neuraminidase (NA) inhibitory activities were evaluated. Most of the compounds have potent NA inhibitory activity. Compound 1g exhibited the best activity against influenza virus A (H1N1) NA with an IC50 of 29.06 μg/mL, and its crystal structure was determined by single-crystal X-ray diffraction.

Catalytic effect of nanosized metal oxides on the knoevenagel reaction

The effect of nanosized metal oxides (Al, Mg, Cu, Ni oxides) on the synthesis of chalcones that are key intermediate in the synthesis of Nitrendipine and Felodipine drugs was examined.

A facile synthesis of trisubstituted alkenes from β-diketones and aldehydes with AlCl3 as catalyst

Preparation of trisubstituted alkenes from low-activity β-diketones and aldehydes with aluminum chloride as catalyst has been studied. The frequently used catalyst AlCl3 is used for the first time to promote this condensation. The procedure is a convenient, low toxicity, and highly efficient method for industrial synthesis of trisubstituted alkenes in high yield. Springer Science+Business Media B.V. 2011.

Catalytic effect of nanosized metal oxides on the Hantzsch reaction

The effect of nanosized copper and aluminum oxides, which have a higher sorption capacity than that of bulk samples, on the Hantzsch reaction was studied. The adsorption of starting benzaldehydes and ethyl acetoacetate on the surface of copper and aluminum nanooxides resulted in the activation of these molecules and accelerated the Hantzsch reaction. In addition, considerable activation of ammonia and intermediates (chalcone and enamine) on the surface of aluminum nanooxide facilitated an increase in the rate and selectivity of the process. The experimental results were used to develop a one-pot method for the preparation of nifedipine and nitrendipine.

Investigation of the antioxidant properties of some new 4-hydroxycoumarin derivatives

The aim of this investigation was to measure the activity of four 4-hydroxycoumarin derivatives - three of them were described before and one was newly synthesized. The substances were ethyl 2-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(4-hydroxyphenyl)methyl]-3-oxobutanoate (SS-14), 4-[1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(ethoxycarbonyl)-3-oxobutyl]benzoic acid (SS-17), ethyl 2-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(3-nitrophenyl)methyl]-3-oxobutanoate (SS-21) and ethyl 2-[(3,4,5-trimethoxyphenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-3-oxobutanoate (T-2). The synthesis of T-2 consists of two steps. First step was Knoevenagel reaction between 3,4,5-trimethoxybenzaldehyde and ethylacetoacetate. Ethyl 2-(3,4,5-trimethoxy)-phenylmethyleneacetoacetate was the product. Second step was Michael addition reaction between the latter product and 4-hydroxycoumarin. All the compounds were tested in vitro for antioxidant activity in hypochlorous system. The assay was based on the luminol-dependent chemiluminescence of free radicals, which decreased in the presence of 4-hydroxycoumarin derivative. Compound SS-14 (ethyl 2-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(4-hydroxyphenyl)methyl]-3-oxobutanoate) expresses the best scavenger activity at the highest concentration (10-4 mol/L).

Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives

Six new 4-hydroxycoumarin derivatives have been synthesized. They were characterized by UV-vis, IR, 1H NMR, 13C NMR, mass spectral data, elemental analysis, TLC and melting point determination. The new 4-hydroxycoumarin derivatives a

Dimethylamine benzoate or p-anisate catalysed process for the preparation of 4-(nitrophenyl)-dihydropyridines

PCT No. PCT/EP96/01090 Sec. 371 Date Aug. 18, 1997 Sec. 102(e) Date Aug. 18, 1997 PCT Filed Mar. 14, 1996 PCT Pub. No. WO96/29310 PCT Pub. Date Sep. 26, 1996A method for the preparation of 4-(nitrophenyl)-dihydro-pyridines by reacting a benzaldehyde with an acetoacetate and reacting the resulting benzylidene derivative with an enamine derivative. Both reactions are catalyzed by dimethylamine benzoate or p-anisate.

Novel 2-amino-1,4-dihydropyridine calcium antagonists. II. Synthesis and antihypertensive effects of 2-amino-1,4-dihydropyridine derivatives having N,N-dialkylaminoalkoxycarbonyl groups at 3- and/or 5-positions

Novel 2-amino-1,4-dihydropyridine derivatives I, which contain N,N-dialkylaminoalkoxycarbonyl groups at the 3- and/or 5-position, were synthesized and their antihypertensive effects were evaluated in spontaneously hypertensive rats. Remarkably prolonged duration of antihypertensive action was observed when a tertiary amino group was introduced into either the 3- or 5-ester side-chain of the 1,4-dihydropyridine ring. In particular, the compounds containing cyclic amino moieties at the 3-position showed greater potency than those with acyclic amino moieties. Chemical modification studies indicated that the two ester side-chains of 1,4-dihydropyridine at the 3- and 5-position might function in a different manner in relation to the antihypertensive activities. 3-(1-Benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxyl ate, I-43 (CS-905), exhibited potent and long-lasting antihypertensive effects with gradual onset of action, and is a promising candidate as an antihypertensive drug.