Diethyl {[(2,3,4-trifluorophenyl)amino]-methylene}malonate

Base Information

• Chemical Name: Diethyl {[(2,3,4-trifluorophenyl)amino]-methylene}malonate
• CAS No.: 100501-60-8
• Molecular Formula: C14H14F3NO4
• Molecular Weight: 317.265
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID601159868
• Nikkaji Number: J135.072B
• Mol file: 100501-60-8.mol

Synonyms:100501-60-8;diethyl {[(2,3,4-trifluorophenyl)amino]methylene}malonate;diethyl 2-[(2,3,4-trifluoroanilino)methylidene]propanedioate;[[(2,3,4-Trifluorophenyl)amino]methylene]propanedioic acid diethyl ester;MFCD00796044;Diethyl ([(2,3,4-trifluorophenyl)amino]methylene)malonate;Diethyl 2-(((2,3,4-trifluorophenyl)amino)methylene)malonate;Diethyl {[(2,3,4-trifluorophenyl)amino]-methylene}malonate;1,3-diethyl 2-{[(2,3,4-trifluorophenyl)amino]methylidene}propanedioate;CBMicro_035050;SCHEMBL8628152;KSWGDSAIUPPJIB-UHFFFAOYSA-N;DTXSID601159868;AKOS005172685;LS-03554;BIM-0034963.P001;CS-0329934;SR-01000221549;SR-01000221549-1;Diethyl2-(((2,3,4-trifluorophenyl)amino)methylene)malonate;2-[(2,3,4-Trifluoroanilino)methylene]malonic acid diethyl ester;1,3-Diethyl 2-[[(2,3,4-trifluorophenyl)amino]methylene]propanedioate;2-((2,3,4-TRIFLUORO-PHENYLAMINO)-METHYLENE)-MALONIC ACID DIETHYL ESTER

Chemical Property of Diethyl {[(2,3,4-trifluorophenyl)amino]-methylene}malonate

Chemical Property:

• PSA: 64.63000
• LogP: 2.59890
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 317.08749241
• Heavy Atom Count: 22
• Complexity: 410

Purity/Quality:

98%min ^*data from raw suppliers

Diethyl {[(2,3,4-trifluorophenyl)amino]-methylene}malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=CNC1=C(C(=C(C=C1)F)F)F)C(=O)OCC

Technology Process of Diethyl {[(2,3,4-trifluorophenyl)amino]-methylene}malonate

There total 1 articles about Diethyl {[(2,3,4-trifluorophenyl)amino]-methylene}malonate 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: 86.0%

2,3,4-trifluoroaniline (3862-73-5) + diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl 2-((2,3,4-trifluorophenylamino)methylene)malonate (100501-60-8)

Guidance literature:

for 2h; Heating;

DOI:10.1016/j.tet.2006.11.079

Reference yield: 85.7%

diethyl 2-((2,3,4-trifluorophenylamino)methylene)malonate (100501-60-8) → ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (79660-46-1)

Guidance literature:

In diphenylether; at 190 ℃; for 0.416667h; Microwave irradiation;

DOI:10.1080/00397910902906503

Reference yield:

diethyl 2-((2,3,4-trifluorophenylamino)methylene)malonate (100501-60-8) → 7-(butylamino)-6,8-difluoro-4-oxo-1-(4-(trifluoromethyl)benzyl)-1,4-dihydroquinoline-3-carboxylic acid (1293992-56-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diphenylether / 8 h / 250 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C

2.2: 4 h / Reflux

3.1: hydrogenchloride; water / acetic acid / 2 h / Reflux

4.1: acetonitrile / 7 h / 90 °C

With hydrogenchloride; water; sodium hydride; In diphenylether; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.ejmech.2011.01.044

upstream raw materials:

2,3,4-trifluoroaniline

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

ethyl 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

7-(4-benzylpiperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

1-ethyl-6,8-difluoro-4-oxo-7-(4-phenylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

Refernces

• 1、 De La Cruz, Angeles,Elguero, Jose,Goya, Pilar,Martinez, Ana,Pfleiderer, Wolfgang. "Tautomerism and acidity in 4-quinolone-3-carboxylic acid derivatives". . p. 6135 - 6150. Retrieved 1992.
• 2、 Azad, Chandra S.,Bhunia, Shome S.,Krishna, Atul,Shukla, Praveen K.,Saxena, Anil K.. "Novel Glycoconjugate of 8-Fluoro Norfloxacin Derivatives as Gentamicin-resistant Staphylococcus aureus Inhibitors: Synthesis and Molecular Modelling Studies". . p. 440 - 446. Retrieved 2015/02/19.
• 3、 Sunduru, Naresh,Gupta, Leena,Chauhan, Kuldeep,Mishra, Nripendra N.,Shukla, Praveen K.,Chauhan, Prem M.S.. "Synthesis and antibacterial evaluation of novel 8-fluoro Norfloxacin derivatives as potential probes for methicillin and vancomycin-resistant Staphylococcus aureus". experimental part. p. 1232 - 1244. Retrieved 2011/04/22.