Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester

Base Information

• Chemical Name: Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester
• CAS No.: 74073-22-6
• Molecular Formula: C12H10Cl2O3
• Molecular Weight: 273.116
• Hs Code.: 2918300090
• Mol file: 74073-22-6.mol

Synonyms:Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester;Methyl 2-(2,3-dichlorobenzylidine)acetoacetate;QQXPSPWWWCQBFM-UHFFFAOYSA-N;AKOS028109843;FT-0671674;D70336;methyl alpha-methylcarbonyl-2,3-dichlorocinnamate;Methyl 2-acetyl-3-(2,3-dichlorophenyl)-acrylate;2-(2,3-dichlorobenzylidene)-acetoacetic acid methyl ester;2-(2,3-Dichlorobenzylidene)-3-oxobutanoic acid methyl ester;2-[(2,3-dichlorophenyl)methylene]-3-oxobutanoic acid, methyl ester

Chemical Property of Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester

Chemical Property:

• Vapor Pressure: 4.35E-06mmHg at 25°C
• Melting Point: 81-83 °C
• Refractive Index: 1.574
• Boiling Point: 383.6 °C at 760 mmHg
• Flash Point: 157.1 °C
• PSA: 43.37000
• Density: 1.337 g/cm³
• LogP: 3.13880
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 272.0006996
• Heavy Atom Count: 17
• Complexity: 339

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-(2,3-Dichlorobenzylidene)acetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(=CC1=C(C(=CC=C1)Cl)Cl)C(=O)OC
• Uses: Methyl 2-(2,3-dichlorobenzylidine)acetoacetate is an intermediate,it is used in the preparation of dihydropyridine calcium antagonists. An intermediate used in the preparation of dihydropyridine calcium antagonists.

Technology Process of Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester

There total 1 articles about Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

acetoacetic acid methyl ester (105-45-3) + 2,3-dichlorobenzylaldehyde (6334-18-5) → (E/Z)-methyl 2-(2,3-dichlorobenzylidene)acetoacetate (74073-22-6)

Guidance literature:

With piperidine; acetic acid; In benzene; for 2h; Heating;

DOI:10.1248/cpb.41.108

Reference yield: 91.32%

(E/Z)-methyl 2-(2,3-dichlorobenzylidene)acetoacetate (74073-22-6) + 3-amino-2-butenoic acid 2-cyanoethyl ester → (+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid (123853-39-4)

Guidance literature:

(E/Z)-methyl 2-(2,3-dichlorobenzylidene)acetoacetate; 3-amino-2-butenoic acid 2-cyanoethyl ester; In isopropyl alcohol; at 35 - 40 ℃; Reflux; Large scale;

With sodium hydroxide; In isopropyl alcohol; Concentration; Large scale;

Reference yield: 86.3%

(E/Z)-methyl 2-(2,3-dichlorobenzylidene)acetoacetate (74073-22-6) + benzyl-β-aminocrotonate (43107-11-5) → 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid-(phenylmethyl) methyl ester

Guidance literature:

In methanol; at 60 ℃; for 3h;

upstream raw materials:

acetoacetic acid methyl ester

2,3-dichlorobenzylaldehyde

Downstream raw materials:

cyclopropylmethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate methyl ester-(2-cyanoethyl)ester

4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(2-hydroxyethoxymethyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

(+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid

Refernces

• 1、 Ogawa,Nakato,Tsuchida,Hatayama. "Synthesis and antihypertensive activities of new 1,4-dihydropyridine derivatives containing a nitrooxy moiety at the 3-ester position". . p. 108 - 116. Retrieved 2007/10/02.