3-(2-Chloroanilino)-3-oxopropanoic acid

Base Information

• Chemical Name: 3-(2-Chloroanilino)-3-oxopropanoic acid
• CAS No.: 15270-55-0
• Molecular Formula: C9H8ClNO3
• Molecular Weight: 213.61800
• DSSTox Substance ID: DTXSID70363275
• Wikidata: Q82146886
• Mol file: 15270-55-0.mol

Synonyms:15270-55-0;3-(2-chloroanilino)-3-oxopropanoic acid;Propanoic acid, 3-[(2-chlorophenyl)amino]-3-oxo-;2-[(2-chlorophenyl)carbamoyl]acetic Acid;Oprea1_117539;SCHEMBL17434797;DTXSID70363275;MFCD00201976;AKOS011514335;2-[(2-chlorophenyl)carbamoyl]aceticAcid;7H-037

Chemical Property of 3-(2-Chloroanilino)-3-oxopropanoic acid

Chemical Property:

• Melting Point: 152-153 °C (decomp)(Solv: ethyl acetate (141-78-6))
• Boiling Point: 468.6±30.0 °C(Predicted)
• PSA: 69.89000
• Density: 1.467±0.06 g/cm3(Predicted)
• LogP: 2.40270
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 213.0192708
• Heavy Atom Count: 14
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-(2-Chloroanilino)-3-oxopropanoic acid

There total 6 articles about 3-(2-Chloroanilino)-3-oxopropanoic acid 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: 94.0%

cycl-isopropylidene malonate (2033-24-1) + o-chloroaniline (95-51-2) → 3-((2-chlorophenyl)amino)-3-oxopropanoic acid (15270-55-0)

Guidance literature:

o-chloroaniline; With chloro-trimethyl-silane; triethylamine; In dichloromethane; for 0.5h; Inert atmosphere; Schlenk technique; Reflux;

cycl-isopropylidene malonate; In dichloromethane; at 30 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.9b00450

Reference yield:

ethyl 3-((2-chlorophenyl)amino)-3-oxopropanoate (15270-54-9) → 3-((2-chlorophenyl)amino)-3-oxopropanoic acid (15270-55-0)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 14h;

Reference yield:

o-chloroaniline (95-51-2) → 3-((2-chlorophenyl)amino)-3-oxopropanoic acid (15270-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 14 h / 130 °C

2: water; sodium hydroxide / tetrahydrofuran / 14 h / 20 °C

With pyridine; water; sodium hydroxide; In tetrahydrofuran;

upstream raw materials:

N-(2-chlorophenyl)acetamide

o-chloroaniline

diethyl malonate

ethyl 3-((2-chlorophenyl)amino)-3-oxopropanoate

Downstream raw materials:

N-(2-chloro-phenyl)-2-(2-methoxy-benzylidene)-malonamic acid

2-methoxy-trans-cinnamic acid-(2-chloro-anilide)

2-benzylidene-N-(2-chloro-phenyl)-malonamic acid

(2E)-N-(2-chlorophenyl)cinnamamide