5-O-(2-hydroxyethyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Base Information

• Chemical Name: 5-O-(2-hydroxyethyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS No.: 85677-95-8
• Molecular Formula: C18H20N2O7
• Molecular Weight: 376.366
• DSSTox Substance ID: DTXSID601116272
• Mol file: 85677-95-8.mol

Synonyms:85677-95-8;SCHEMBL7431297;DTXSID601116272;AKOS016035637;3-(2-Hydroxyethyl) 5-methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Chemical Property of 5-O-(2-hydroxyethyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Chemical Property:

• Melting Point: 176-178 °C(Solv: methanol (67-56-1); isopropanol (67-63-0))
• Boiling Point: 548.8±50.0 °C(Predicted)
• PSA: 130.68000
• Density: 1.314±0.06 g/cm3(Predicted)
• LogP: 2.39010
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 376.12705098
• Heavy Atom Count: 27
• Complexity: 678

Purity/Quality:

99% ^*data from raw 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)OCCO)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OC

Technology Process of 5-O-(2-hydroxyethyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

There total 6 articles about 5-O-(2-hydroxyethyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 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: 96.0%

3-nitrobenzylideneacetoacetic acid 2-chloroethyl ester + methyl 3-aminocrotonate (21731-17-9) → 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester (54527-89-8) + 2-hydroxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (85677-95-8)

Guidance literature:

molecular sieve; In chloroform;

Reference yield: 46.3%

5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (74936-72-4) + 2-bromoethanol (540-51-2) → 2-hydroxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (85677-95-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 12h; Ambient temperature;

DOI:10.1248/cpb.41.108

Reference yield:

3-nitro-benzaldehyde (99-61-6) → 2-hydroxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (85677-95-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 28 percent / ethanol / 12 h / Heating

2: 73 percent / dimethylformamide / 20 h / Heating

3: 67 percent / NaOH / H₂O; 1,2-dimethoxy-ethane / 3 h / Ambient temperature

With sodium hydroxide; In 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide;

upstream raw materials:

mono(acetoacetate)ethylene glycol

3-nitro-benzaldehyde

methyl 3-aminocrotonate

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

Downstream raw materials:

Nicardipine

nicardipine hydrochloride

2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-methyl ester 5-[2-(toluene-4-sulfonyloxy)-ethyl] ester

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