Ethyl 4,5-dioxo-1-phenylpyrrolidine-3-carboxylate

Base Information

• Chemical Name: Ethyl 4,5-dioxo-1-phenylpyrrolidine-3-carboxylate
• CAS No.: 5336-49-2
• Molecular Formula: C13H13NO4
• Molecular Weight: 247.2466
• NSC Number: 333
• DSSTox Substance ID: DTXSID50277003
• Mol file: 5336-49-2.mol

Synonyms:ethyl 4,5-dioxo-1-phenylpyrrolidine-3-carboxylate;5336-49-2;NSC333;DTXSID50277003;NSC 333;NSC-333

Chemical Property of Ethyl 4,5-dioxo-1-phenylpyrrolidine-3-carboxylate

Chemical Property:

• Vapor Pressure: 1.49E-05mmHg at 25°C
• Boiling Point: 366.2°Cat760mmHg
• Flash Point: 175.3°C
• Density: 1.293g/cm³
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 247.08445790
• Heavy Atom Count: 18
• Complexity: 360

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CN(C(=O)C1=O)C2=CC=CC=C2

Technology Process of Ethyl 4,5-dioxo-1-phenylpyrrolidine-3-carboxylate

There total 5 articles about Ethyl 4,5-dioxo-1-phenylpyrrolidine-3-carboxylate 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:

ethyl 3-phenylaminopropionate (62750-11-2) + oxalic acid diethyl ester (95-92-1) → 1-phenyl-4-carboethoxy-2,3-dioxo-pyrrolidine (5336-49-2)

Guidance literature:

With sodium ethanolate;

DOI:10.1021/ja01110a034

Reference yield:

aniline (62-53-3) + ethyl acrylate (140-88-5,9003-32-1) → 1-phenyl-4-carboethoxy-2,3-dioxo-pyrrolidine (5336-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / ethanol / 24 h / Reflux

2: sodium ethanolate / 1 h / Reflux

With sodium ethanolate; acetic acid; In ethanol;

DOI:10.1039/c9ob02663k

Reference yield:

ethyl acrylate (140-88-5,9003-32-1) → 1-phenyl-4-carboethoxy-2,3-dioxo-pyrrolidine (5336-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / ethanol / 24 h / Reflux

2: sodium; ethanol / 1 h / Reflux

With ethanol; sodium; acetic acid; In ethanol;

DOI:10.1021/acs.joc.8b01057

upstream raw materials:

ethyl 3-phenylaminopropionate

oxalic acid diethyl ester

ethyl acrylate

aniline

Downstream raw materials:

1-phenyl-pyrrolidine-2,3-dione

4,5-Dioxo-1-phenyl-pyrrolidine-3-carboxylic acid methyl-(4-phenylsulfanyl-phenyl)-amide

(E)-4-benzylidene-1-phenylpyrrolidine-2,3-dione