3-(3-Nitrophenyl)-4-pyridinecarboxylic acid ethyl ester

Base Information

• Chemical Name: 3-(3-Nitrophenyl)-4-pyridinecarboxylic acid ethyl ester
• CAS No.: 252921-32-7
• Molecular Formula: C14H12 N2 O4
• Molecular Weight: 272.26
• DSSTox Substance ID: DTXSID80469838
• Wikidata: Q82297729
• Mol file: 252921-32-7.mol

Synonyms:252921-32-7;3-(3-NITROPHENYL)-4-PYRIDINECARBOXYLIC ACID ETHYL ESTER;Ethyl 3-(3-nitrophenyl)pyridine-4-carboxylate;SCHEMBL6437170;DTXSID80469838;JHRPBJPYOUEUBO-UHFFFAOYSA-N;FT-0613622;5-(3-nitrophenyl)-4-pyridinecarboxyiic acid ethyl ester

Chemical Property of 3-(3-Nitrophenyl)-4-pyridinecarboxylic acid ethyl ester

Chemical Property:

• PSA: 85.01000
• LogP: 3.35670
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 272.07970687
• Heavy Atom Count: 20
• Complexity: 356

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C=NC=C1)C2=CC(=CC=C2)[N+](=O)[O-]

Technology Process of 3-(3-Nitrophenyl)-4-pyridinecarboxylic acid ethyl ester

There total 1 articles about 3-(3-Nitrophenyl)-4-pyridinecarboxylic acid ethyl 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: 30.0%

ethanol (64-17-5) + m-nitrobenzene boronic acid (13331-27-6) + methyl 3-iodo-4-pyridinecarboxylate (188677-49-8) → ethyl 3-(3-nitrophenyl)-4-pyridinecarboxylate (252921-32-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In toluene; at 90 ℃; for 24h;

DOI:10.1021/jm0509445

Reference yield: 81.0%

ethyl 3-(3-nitrophenyl)-4-pyridinecarboxylate (252921-32-7) → 5-(3-aminophenyl)-4-pyridinecarboxylic acid ethyl ester (252921-31-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1021/jm0509445

Reference yield:

ethyl 3-(3-nitrophenyl)-4-pyridinecarboxylate (252921-32-7) → 3-(3-{2-[(R)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-ethylamino}-phenyl)-isonicotinic acid

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / H₂ / Pd/C / ethyl acetate

2: 85 percent / AcOH; NaBH(OAc)3 / CH₂Cl₂

3: HCl / dioxane; CH₂Cl₂ / 16 h / 20 °C

4: 180.7 mg / LiOH*H₂O / methanol; H₂O / 3 h

With hydrogenchloride; lithium hydroxide; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm0509445

upstream raw materials:

ethanol

m-nitrobenzene boronic acid

methyl 3-iodo-4-pyridinecarboxylate

Downstream raw materials:

5-(3-aminophenyl)-4-pyridinecarboxylic acid ethyl ester