4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid

Base Information

• Chemical Name: 4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid
• CAS No.: 123853-39-4
• Molecular Formula: C16H15Cl2NO4
• Molecular Weight: 356.205
• UNII: 446669RI9H
• DSSTox Substance ID: DTXSID30383176
• Nikkaji Number: J826.431G
• Wikidata: Q27258714
• Mol file: 123853-39-4.mol

Synonyms:4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid;123853-39-4;105580-45-8;H-152/81;4-(2,3-dichlorophenyl)-5-methoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic Acid;4-(2,3-DICHLORO-PHENYL)-2,6-DIMETHYL-1,4-DIHYDRO-PYRIDINE-3,5-DICARBOXYLIC ACID MONOMETHYL ESTER;UNII-446669RI9H;MFCD06654363;3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl ester;446669RI9H;Desethyl Felodipine;C16H15Cl2NO4;SCHEMBL820019;DTXSID30383176;LHAOQTPGTBGTIG-UHFFFAOYSA-N;AMY23255;BCP09129;AKOS015901816;CS-W009229;AC-27027;DS-14947;SY028070;FT-0696469;F19511;A890642;A898881;Q27258714;2,6-dimethyl-3-carbomethoxy-4-(2,3-dichlorophenyl)-5-carboxy-1,4-dihydropyridine;1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(2,3-dichlorophenyl)pyridine-3-carboxylic acid;4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester;4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylicacid

Chemical Property of 4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid

Chemical Property:

• Melting Point: 197-200°C
• Boiling Point: 483.0±45.0 °C(Predicted)
• PKA: 1.65±0.70(Predicted)
• PSA: 75.63000
• Density: 1.375±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 3.81460
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 355.0378133
• Heavy Atom Count: 23
• Complexity: 585

Purity/Quality:

98%, ^*data from raw suppliers

Desethyl Felodipine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OC)C2=C(C(=CC=C2)Cl)Cl)C(=O)O
• Uses: Desethyl Felodipine is an impurity in the synthesis of Felodipine (F232375), a dihydropyridine calcium channel blocker.

Technology Process of 4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid

There total 27 articles about 4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid 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: 99.0%

4-(-2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid methyl ester (91189-59-2) → (+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid (123853-39-4)

Guidance literature:

With methanesulfonic acid; at 80 ℃; for 3h; Temperature;

Reference yield: 96.7%

4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid-(phenylmethyl) methyl ester → (+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid (123853-39-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 30 ℃; for 8h;

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;

upstream raw materials:

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

acetoacetic acid methyl ester

2,3-dichlorobenzylaldehyde

(E/Z)-methyl 2-(2,3-dichlorobenzylidene)acetoacetate

Downstream raw materials:

clevidipine

(S)-4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-((R)-carboxy-phenyl-methyl) ester 5-methyl ester

(R)-4-(2,3-Dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-((R)-carboxy-phenyl-methyl) ester 5-methyl ester

5-Chlorocarbonyl-4-(2,3-dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid methyl ester

Refernces

• 1、 -. "Novel synthesis method of clevidipine butyrate important intermediate". Paragraph 0021. . Retrieved 2016/10/07.
• 2、 -. "Compound and its as L-type calcium channel blocker or/and application of acetylcholine esterase inhibitors". . . Retrieved 2016/10/07.