ethyl α-carbethoxy-β-m-bromoanilinoacrylate

Base Information

• Chemical Name: ethyl α-carbethoxy-β-m-bromoanilinoacrylate
• CAS No.: 351893-47-5
• Molecular Formula: C₁₄H₁₆BrNO₄
• Molecular Weight: 342.189
• Mol file: 351893-47-5.mol

Synonyms:ethyl α-carbethoxy-β-m-bromoanilinoacrylate

Chemical Property of ethyl α-carbethoxy-β-m-bromoanilinoacrylate

Chemical Property:

• Melting Point: 70-71 °C
• Boiling Point: 372.9±42.0 °C(Predicted)
• Density: 1.419±0.06 g/cm3(Predicted)

Purity/Quality:

2-[[(3-Bromophenyl)amino]methylene]propanedioicAcid1,3-DiethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2-[[(3-Bromophenyl)amino]methylene]propanedioic Acid 1,3-Diethyl Ester is an intermediate in the synthesis of Rosoxacin (R693580), an antibacterial agent used against Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Staphylococcus aureus and Streptococcus pneumoniae.

Technology Process of ethyl α-carbethoxy-β-m-bromoanilinoacrylate

There total 1 articles about ethyl α-carbethoxy-β-m-bromoanilinoacrylate 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: 100.0%

diethyl 2-ethoxymethylenemalonate (87-13-8) + m-Bromoaniline (591-19-5) → ethyl α-carbethoxy-β-m-bromoanilinoacrylate (351893-47-5)

Guidance literature:

at 90 - 110 ℃; for 1h;

DOI:10.1021/jm980146x

Reference yield: 88.0%

ethyl α-carbethoxy-β-m-bromoanilinoacrylate (351893-47-5) → 7-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (208580-23-8,179943-57-8)

Guidance literature:

In diphenylether; at 235 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmc.2019.06.006

Reference yield:

ethyl α-carbethoxy-β-m-bromoanilinoacrylate (351893-47-5) + trifluoroacetic acid (76-05-1) → N-(5-bromo-2-hydroxyphenyl)-2,2,2-trifluoroacetamide (1638101-80-0)

Guidance literature:

With Oxone; In 1,4-dioxane; at 90 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.05.042

upstream raw materials:

diethyl 2-ethoxymethylenemalonate

m-Bromoaniline

Downstream raw materials:

ethyl 7-bromo-4-hydroxyquinoline-3-carboxylate

4-hydroxy-7-bromoquinoline

7-bromo-4-hydroxy-3-quinolinecarboxylic acid

7-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

Refernces

• 1、 Simeone,Iorio,Siebert,Rehman,Schnürch,Mihovilovic,Ernst. "Defined concatenated α6α1β3γ2 GABAA receptor constructs reveal dual action of pyrazoloquinolinone allosteric modulators". supporting information. p. 3167 - 3178. Retrieved 2019/06/17.
• 2、 Berninger, Michael,Erk, Christine,Fu?, Antje,Skaf, Joseph,Al-Momani, Ehab,Israel, Ina,Raschig, Martina,Güntzel, Paul,Samnick, Samuel,Holzgrabe, Ulrike. "Fluorine walk: The impact of fluorine in quinolone amides on their activity against African sleeping sickness". supporting information. p. 377 - 391. Retrieved 2018/05/22.