Methyl 2-(4-chloroanilino)-2-oxoacetate

Base Information

• Chemical Name: Methyl 2-(4-chloroanilino)-2-oxoacetate
• CAS No.: 41374-66-7
• Molecular Formula: C9H8ClNO3
• Molecular Weight: 213.62
• DSSTox Substance ID: DTXSID00393888
• Nikkaji Number: J1.237.346E
• Mol file: 41374-66-7.mol

Synonyms:methyl 2-(4-chloroanilino)-2-oxoacetate;41374-66-7;methyl 4-chlorophenylamino-oxo-acetate;SCHEMBL5548239;DTXSID00393888;DVCNIZWLRANNMP-UHFFFAOYSA-N;AKOS024279633;FT-0740160;N-(4-Chlorophenyl)oxamidic acid methyl ester

Chemical Property of Methyl 2-(4-chloroanilino)-2-oxoacetate

Chemical Property:

• PSA: 58.89000
• LogP: 2.10100
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 213.0192708
• Heavy Atom Count: 14
• Complexity: 224

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=O)NC1=CC=C(C=C1)Cl

Technology Process of Methyl 2-(4-chloroanilino)-2-oxoacetate

There total 10 articles about Methyl 2-(4-chloroanilino)-2-oxoacetate 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: 95.0%

monomethyl oxalyl chloride (5781-53-3) + 4-chloro-aniline (106-47-8) → methyl 2-[(4-chlorophenyl)amino]-2-oxoacetate (41374-66-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2020.127744

Reference yield: 80.0%

methanol (67-56-1) + 4'-Chloroacetoacetanilide (101-92-8) → methyl 2-[(4-chlorophenyl)amino]-2-oxoacetate (41374-66-7)

Guidance literature:

With [bis(acetoxy)iodo]benzene; copper(l) chloride; at 25 ℃; for 3h;

DOI:10.1002/adsc.201800616

Reference yield: 61.0%

C12H12ClNO4 (87748-34-3) → dimethyl 6-chloroquinoxaline-2,3-dicarboxylate (1458011-77-2) + methyl 2-[(4-chlorophenyl)amino]-2-oxoacetate (41374-66-7)

Guidance literature:

With sodium azide; [bis(acetoxy)iodo]benzene; In 1,2-dichloro-ethane; at 0 - 28 ℃;

DOI:10.1039/c6ob00447d

upstream raw materials:

methanol

N-(4-chlorophenyl)-2,2,2,-trichloroacetamide

monomethyl oxalyl chloride

4-chloro-aniline

Downstream raw materials:

1-(4-chlorophenyl)indoline-2,3-dione

Refernces

• 1、 Gediya, Shweta K.,Vyas, Vijyesh K.,Clarkson, Guy J.,Wills, Martin. "Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides". supporting information. p. 7803 - 7807. Retrieved 2021/10/20.
• 2、 Zhang, Zhiguo,Gao, Xiaolong,Yu, Haifeng,Zhang, Guisheng,Liu, Jianming. "Copper-Catalysed (Diacetoxyiodo)benzene-Promoted Aerobic Esterification Reaction: Synthesis of Oxamates from Acetoacetamides". supporting information. p. 3406 - 3411. Retrieved 2018/07/31.