5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

Base Information

• Chemical Name: 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid
• CAS No.: 74936-72-4
• Molecular Formula: C16H16N2O6
• Molecular Weight: 332.313
• Hs Code.: 2933399090
• European Community (EC) Number: 278-034-2
• UNII: 5DU0E310OI
• DSSTox Substance ID: DTXSID10996440
• Nikkaji Number: J331.416B
• Wikidata: Q27261893
• ChEMBL ID: CHEMBL1098515
• Mol file: 74936-72-4.mol

Synonyms:1,4-dihydro-2,6-dimethyl-4--(3-nitrophenyl)pyridine-3-carboxylic acid-5-carboxylic methyl ester;carboxy-nifedipine

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

Chemical Property:

• Vapor Pressure: 5.1E-11mmHg at 25°C
• Melting Point: 200-202oC
• Refractive Index: 1.587
• Boiling Point: 505 °C at 760 mmHg
• PKA: 1.66±0.70(Predicted)
• Flash Point: 259.2 °C
• PSA: 121.45000
• Density: 1.345 g/cm³
• LogP: 2.93920
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Sparingly), Methanol (Slightly, Heated)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 332.10083623
• Heavy Atom Count: 24
• Complexity: 631

Purity/Quality:

99%min ^*data from raw suppliers

1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylicAcid3-MethylEster ^*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=CC(=CC=C2)[N+](=O)[O-])C(=O)O
• Uses: 1,4-Dihydropyridine derivative used in the prevention and therapy of atherosclerotic degradation of arterial walls. Nicardipine USP Related Compound A. 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester can be used in the prevention and therapy of atherosclerotic degradation of arterial walls.

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

There total 28 articles about 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-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: 88.0%

2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester (75130-24-4) → 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (74936-72-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; for 5h; Ambient temperature;

DOI:10.1248/cpb.42.1579

Reference yield: 84.5%

m-nifedipine (21881-77-6) → 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (74936-72-4)

Guidance literature:

With water; sodium hydroxide; In methanol; at 40 - 60 ℃;

Reference yield: 83.0%

2-acetoacetic acid (541-50-4) + 3-nitro-benzaldehyde (99-61-6) + methyl 3-aminocrotonate (14205-39-1) → 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (74936-72-4)

Guidance literature:

With polyphosphoric acid; In ethanol; Reflux; Inert atmosphere;

DOI:10.2174/1386207318666150525093659

upstream raw materials:

2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Nicardipine

(R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-((S)-1-benzyl-piperidin-3-yl) ester 5-methyl ester

Downstream raw materials:

SL 5721

1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride

2-hydroxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

lercanidipine