2,6-Dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid monomethyl ester

Base Information

• Chemical Name: 2,6-Dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid monomethyl ester
• CAS No.: 64603-72-1
• Molecular Formula: C16H14 N2 O6
• Molecular Weight: 330.297
• UNII: CTJ52M7FQT
• Nikkaji Number: J331.427H
• Mol file: 64603-72-1.mol

Synonyms:64603-72-1;2,6-Dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid monomethyl ester;5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3-carboxylic Acid;CTJ52M7FQT;SCHEMBL4384277;SL-5721;2,6-Dimethyl-4-(3-nitro-phenyl)-pyridine-3,5-dicarboxylic acid monomethyl ester;5-(METHOXYCARBONYL)-2,6-DIMETHYL-4-(3-NITROPHENYL)PYRIDINE-3-CARBOXYLIC ACID;NS00116482;3-Methyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate;5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid;2,?6-?Dimethyl-?4-?(3-?nitrophenyl)?pyridine-?3,?5-?dicarboxylic acid monomethyl ester;3,5-Pyridinedicarboxylic acid, 2,6-dimethyl-4-(3-nitrophenyl)-, monomethyl ester

Chemical Property of 2,6-Dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid monomethyl ester

Chemical Property:

• Melting Point: 196-198 °C(Solv: methanol (67-56-1))
• Boiling Point: 475.2±45.0 °C(Predicted)
• PKA: 1.05±0.25(Predicted)
• PSA: 122.31000
• Density: 1.360±0.06 g/cm3(Predicted)
• LogP: 3.28160
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 330.08518617
• Heavy Atom Count: 24
• Complexity: 505

Purity/Quality:

>95% ^*data from raw suppliers

2,?6-?Dimethyl-?4-?(3-?nitrophenyl)?pyridine-?3,?5-?dicarboxylicacidmonomethylester ^*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: 2,?6-?Dimethyl-?4-?(3-?nitrophenyl)?pyridine-?3,?5-?dicarboxylic acid monomethyl ester is an impurity of Nicardipine, a dihydropyridine calcium channel blocker that is used to treat high blood pressure and angina.

Technology Process of 2,6-Dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid monomethyl ester

There total 5 articles about 2,6-Dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid monomethyl 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: 94.0%

5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (74936-72-4) → SL 5721 (64603-72-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetone; for 0.166667h; Ambient temperature;

DOI:10.1055/s-1990-26982

Reference yield:

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester (39562-70-4) → SL 5721 (64603-72-1) + 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (74936-72-4) + methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydro-furo<3,4-b>pyridine-3-carboxylate (64603-74-3) + ethyl-2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro<3,4-b>3-pyridinecarboxylate (89288-25-5) + (R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-((2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl) ester 5-methyl ester (138135-46-3) + (S)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-((2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl) ester 5-methyl ester (138135-45-2)

Guidance literature:

biotransformation in rat, dog, and mouse (in vivo and in vitro);

Reference yield:

Dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (76258-20-3) → SL 5721 (64603-72-1)

Guidance literature:

With potassium hydroxide; In methanol; for 18h; Yield given; Heating;

DOI:10.1248/cpb.28.2609

upstream raw materials:

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

Dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

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

4-methyleneoxetan-2-one

Downstream raw materials:

2,6-dimethyl-5-methoxycarbonyl-4-(m-nitrophenyl)pyridine-3-carboxylic acid N-oxide

carboxymethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylate

methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydro-furo<3,4-b>pyridine-3-carboxylate

ethoxycarbonyl methyl 2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylate

Refernces

• 1、 Scherling,Karl,Ahr,Kern,Siefert. "Biotransformation of nitrendipine in rat, dog, and mouse". . p. 1009 - 1021. Retrieved 2007/10/02.
• 2、 Shibanuma,Iwanami,Fujimoto,et al.. "Synthesis of the metabolites of 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride (nicardipine hydrochloride, YC-93)". . p. 2609 - 2613. Retrieved 2007/10/02.