2-[(3-Methoxyphenylamino)-methylene]malonic acid diethyl ester

Base Information

• Chemical Name: 2-[(3-Methoxyphenylamino)-methylene]malonic acid diethyl ester
• CAS No.: 56881-19-7
• Molecular Formula: C15H19NO5
• Molecular Weight: 293.32
• DSSTox Substance ID: DTXSID30397874
• Mol file: 56881-19-7.mol

Synonyms:56881-19-7;2-[(3-METHOXYPHENYLAMINO)-METHYLENE]MALONIC ACID DIETHYL ESTER;STK006569;SCHEMBL10859696;DTXSID30397874;KNOHETYLDBIVCH-UHFFFAOYSA-N;AKOS003239315;FT-0712899;diethyl 2-((3-methoxyphenylamino)methylene)malonate;Diethyl 2-(((3-methoxyphenyl)amino)methylene)malonate;2-[(3-methoxyphenylamino)-methylene]malonicaciddiethylester;diethyl {[(3-methoxyphenyl)amino]methylidene}propanedioate

Chemical Property of 2-[(3-Methoxyphenylamino)-methylene]malonic acid diethyl ester

Chemical Property:

• PSA: 73.86000
• LogP: 2.19020
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 293.12632271
• Heavy Atom Count: 21
• Complexity: 360

Purity/Quality:

97% ^*data from raw suppliers

2-[(3-METHOXYPHENYLAMINO)METHYLENE]MALONIC ACID DIETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 2-[(3-Methoxyphenylamino)-methylene]malonic acid diethyl ester

There total 2 articles about 2-[(3-Methoxyphenylamino)-methylene]malonic acid diethyl 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: 100.0%

m-Anisidine (536-90-3,918666-97-4) + diethyl 2-ethoxymethylenemalonate (87-13-8) → Diethyl 2-<(3-methoxyphenylamino)methylene>malonate (56881-19-7)

Guidance literature:

at 90 - 110 ℃; for 1h;

DOI:10.1021/jm980146x

Reference yield:

→ Diethyl 2-<(3-methoxyphenylamino)methylene>malonate (56881-19-7)

Guidance literature:

DOI:10.1021/jm00218a003

Reference yield: 89.0%

Diethyl 2-<(3-methoxyphenylamino)methylene>malonate (56881-19-7) → 2-[(3-methoxy-phenylamino)-methylene]-malonic acid monoethyl ester (1415327-25-1)

Guidance literature:

With boron trifluoride diethyl etherate; In chloroform; at 20 ℃; for 0.416667h; chemoselective reaction; Inert atmosphere;

DOI:10.1055/s-0031-1290449

upstream raw materials:

m-Anisidine

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

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

ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate

Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate

4-hydroxy-7-methoxyquinoline

Refernces

• 1、 Chen, Nan-Ying,Gu, Zi-Yu,Li, Xiao-Juan,Liao, Hao-Ran,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa,Yuan, Jing-Mei,Zhang, Guo-Hai. "3-(Benzo[: D] thiazol-2-yl)-4-aminoquinoline derivatives as novel scaffold topoisomerase i inhibitor via DNA intercalation: Design, synthesis, and antitumor activities". . p. 11203 - 11214. Retrieved 2020/07/15.
• 2、 Li, Shangze,Hu, Lihua,Li, Jianru,Zhu, Jiongchang,Zeng, Feng,Huang, Qiuhua,Qiu, Liqin,Du, Runlei,Cao, Rihui. "Design, synthesis, structure-activity relationships and mechanism of action of new quinoline derivatives as potential antitumor agents". . p. 666 - 678. Retrieved 2018/11/30.