Ethyl 3-(4-nitroanilino)-3-oxopropanoate

Base Information

• Chemical Name: Ethyl 3-(4-nitroanilino)-3-oxopropanoate
• CAS No.: 10390-08-6
• Molecular Formula: C11H12N2O5
• Molecular Weight: 252.227
• DSSTox Substance ID: DTXSID60508633
• Wikidata: Q82365729
• Mol file: 10390-08-6.mol

Synonyms:Ethyl 3-(4-nitroanilino)-3-oxopropanoate;10390-08-6;SCHEMBL10631099;DTXSID60508633;MWYYWXZHCBCYII-UHFFFAOYSA-N;AKOS003494358;ethyl 3-[(4-nitrophenyl)amino]-3-oxopropanoate

Chemical Property of Ethyl 3-(4-nitroanilino)-3-oxopropanoate

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 252.07462149
• Heavy Atom Count: 18
• Complexity: 318

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)NC1=CC=C(C=C1)[N+](=O)[O-]

Technology Process of Ethyl 3-(4-nitroanilino)-3-oxopropanoate

There total 10 articles about Ethyl 3-(4-nitroanilino)-3-oxopropanoate 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: 78.0%

diazoacetic acid ethyl ester (623-73-4) + carbon monoxide (201230-82-2) + 4-nitro-aniline (100-01-6,104810-17-5) → ethyl 3-((4-nitrophenyl)amino)-3-oxopropanoate (10390-08-6) + N-(4'-nitrophenyl)-2-amino-ethylacetate (3589-59-1)

Guidance literature:

With C₁₅H₂₂N₂Rh⁽¹⁺⁾*F₆P^(1-); potassium carbonate; In toluene; at 60 ℃; for 20h; under 15001.5 Torr; Autoclave; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejic.201501302

Reference yield: 74.0%

4-nitro-aniline (100-01-6,104810-17-5) + diethyl malonate (105-53-3) → ethyl 3-((4-nitrophenyl)amino)-3-oxopropanoate (10390-08-6)

Guidance literature:

at 150 ℃; for 12h;

DOI:10.1016/S0960-894X(02)00028-8

Reference yield: 72.0%

diazoacetic acid ethyl ester (623-73-4) + carbon monoxide (201230-82-2) + 4-nitro-aniline (100-01-6,104810-17-5) → ethyl 3-((4-nitrophenyl)amino)-3-oxopropanoate (10390-08-6)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 60 ℃; for 6h; under 760.051 Torr;

DOI:10.1021/ja107351d

upstream raw materials:

4-nitro-aniline

diethyl malonate

3,3-Diethoxy-acrylsaeure-(4-nitro-anilid)

4-Nitrophenyl isocyanate

Downstream raw materials:

N-(4-nitro-phenyl)-malonamide

3-hydrazinyl-N-(4-nitrophenyl)-3-oxo-propanamide

4-hydroxy-6-nitroquinolin-2(1H)-one

2,4-dichloro-6-nitroquinoline