Diethyl 2-[(3,4-dichloroanilino)methylene]malonate

Base Information

• Chemical Name: Diethyl 2-[(3,4-dichloroanilino)methylene]malonate
• CAS No.: 26832-89-3
• Molecular Formula: C14H15Cl2NO4
• Molecular Weight: 332.183
• European Community (EC) Number: 661-596-1
• Mol file: 26832-89-3.mol

Synonyms:diethyl 2-[(3,4-dichloroanilino)methylene]malonate;Diethyl 2-(((3,4-dichlorophenyl)amino)methylene)malonate;diethyl 2-[(3,4-dichloroanilino)methylidene]propanedioate;26832-89-3;SCHEMBL10862238;STK017348;AKOS000613150;CS-0336108;SR-01000510963;SR-01000510963-1;diethyl {[(3,4-dichlorophenyl)amino]methylidene}propanedioate;1,3-DIETHYL 2-{[(3,4-DICHLOROPHENYL)AMINO]METHYLIDENE}PROPANEDIOATE

Chemical Property of Diethyl 2-[(3,4-dichloroanilino)methylene]malonate

Chemical Property:

• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 331.0378133
• Heavy Atom Count: 21
• Complexity: 380

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diethyl 2-[(3,4-dichloroanilino)methylene]malonate

There total 2 articles about Diethyl 2-[(3,4-dichloroanilino)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:

diethyl 2-ethoxymethylenemalonate (87-13-8) + m,p-dichloroaniline (95-76-1) → diethyl 2-(((3,4 -dichlorophenyl)amino)methylene)malonate (26832-89-3)

Guidance literature:

at 115 - 120 ℃; Yield given; 30-60 min;

DOI:10.1002/(SICI)1097-458X(199611)34:11<972::AID-OMR994>3.0.CO;2-9

Reference yield:

→ diethyl 2-(((3,4 -dichlorophenyl)amino)methylene)malonate (26832-89-3)

Guidance literature:

Reference yield:

diethyl 2-(((3,4 -dichlorophenyl)amino)methylene)malonate (26832-89-3) → ethyl 2-([1,1'-biphenyl]-3-yl)-6,7-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxylate (1373767-31-7)

Guidance literature:

Multi-step reaction with 6 steps

1: diphenylether / Reflux

2: trichlorophosphate / 1,4-dioxane / 1 h / 120 °C

3: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / 24 °C

4: phosphorus(V) oxybromide / chloroform / 1 h / 24 °C

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / 1,4-dioxane; water / 3 h / 75 °C

6: acetic acid / water / 1 h / 120 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; phosphorus(V) oxybromide; In 1,4-dioxane; diphenylether; chloroform; water; 5: Suzuki coupling;

DOI:10.1021/jm201642z

upstream raw materials:

diethyl 2-ethoxymethylenemalonate

m,p-dichloroaniline

Downstream raw materials:

ethyl 2-([1,1'-biphenyl]-3-yl)-6,7-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxylate

ethyl 6,7-dichloro-2-(3-methoxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

ethyl 6,7-dichloro-4-oxo-2-(3-phenoxyphenyl)-1,4-dihydroquinoline-3-carboxylate