4-(3-Nitrophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester

Base Information

• Chemical Name: 4-(3-Nitrophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester
• CAS No.: 75530-60-8
• Molecular Formula: C19H20N2O7
• Molecular Weight: 388.377
• DSSTox Substance ID: DTXSID00464941
• Nikkaji Number: J243.059B
• Mol file: 75530-60-8.mol

Synonyms:75530-60-8;4-(3-Nitrophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester;3-O-methyl 5-O-propan-2-yl 2-formyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;5-Isopropyl-3-methyl 2-formyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate;CID 11406591;5-Isopropyl 3-methyl 2-formyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;3-methyl 5-propan-2-yl 2-formyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;SCHEMBL7428771;DTXSID00464941;AKOS030255501;FT-0672870;4-(3-Nitrophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Me;isopropyl 2-formyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate

Chemical Property of 4-(3-Nitrophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester

Chemical Property:

• Melting Point: 144-146 °C
• PSA: 127.52000
• Density: 1.328 g/cm³
• LogP: 2.98520
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 388.12705098
• Heavy Atom Count: 28
• Complexity: 733

Purity/Quality:

99% ^*data from raw suppliers

4-(3-Nitrophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylicAcid5-IsopropylEster3-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=O)C(=O)OC)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OC(C)C
• Uses: Nilvadipene analogue

Technology Process of 4-(3-Nitrophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-Methyl Ester

There total 6 articles about 4-(3-Nitrophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic Acid 5-Isopropyl Ester 3-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: 95.4%

isopropyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate (75530-94-8) → isopropyl 2-formyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate (75530-60-8)

Guidance literature:

With hydrogenchloride; In acetone; for 1h; Ambient temperature;

DOI:10.1248/cpb.39.3189

Reference yield:

4,4-dimethoxy-3-oxo-butyric acid methyl ester (60705-25-1) → isopropyl 2-formyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate (75530-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: piperidine / benzene / 5 h / Heating

2: 3 h / 100 - 120 °C

3: 6N HCl / acetone / 3 h / 20 °C

With piperidine; hydrogenchloride; In acetone; benzene;

DOI:10.1016/S0040-4020(02)00542-2

Reference yield:

isopropyl 3-aminocrotonate (14205-46-0) → isopropyl 2-formyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate (75530-60-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 3 h / 100 - 120 °C

2: 6N HCl / acetone / 3 h / 20 °C

With hydrogenchloride; In acetone;

DOI:10.1016/S0040-4020(02)00542-2

upstream raw materials:

isopropyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate

4,4-dimethoxy-3-oxo-butyric acid methyl ester

isopropyl 3-aminocrotonate

3-nitro-benzaldehyde

Downstream raw materials:

nilvadipine

isopropyl 2-hydroxymethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3-methoxycarbonyl-5-piperidinecarboxylate

Refernces

• 1、 Chudik, Miloslav,Marchalin, Stefan,Pham-Huu, Duy-Phong,Humpa, Otakar,Friedl, Zdenek. "A simple and expeditious synthesis of substituted 3-aminoindolizines". . p. 1241 - 1252. Retrieved 2007/10/03.