5416-11-5

Basic information

• Product Name: ETHYL (4-NITROPHENYLAMINO) OXOACETATE
• Synonyms: ETHYL (4-NITROPHENYLAMINO) OXOACETATE;2-[(4-Nitrophenyl)aMino]-2-oxo-acetic Acid Ethyl Ester;4'-Nitro-oxanilic Acid Ethyl Ester;N-(4-Nitrophenyl)oxaMic Acid Ethyl Ester;NSC 11343;NSC 55318;Oxalic Acid Monoethyl Ester N-(4-Nitrophenyl)aMide
• CAS NO: 5416-11-5
• Molecular Formula: C₁₀H₁₀N₂O₅
• Molecular Weight: 238.2
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 5416-11-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 172-173°C
• Appearance: /
• Density: 1.394g/cm³
• Refractive Index: 1.595
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: ETHYL (4-NITROPHENYLAMINO) OXOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (4-NITROPHENYLAMINO) OXOACETATE(5416-11-5)
• EPA Substance Registry System: ETHYL (4-NITROPHENYLAMINO) OXOACETATE(5416-11-5)

Safety Data

• Hazardous Substances Data: 5416-11-5(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Crystalline Solid

Uses

Ethyl (4-Nitrophenylamino) Oxoacetate (cas# 5416-11-5) is a compound useful in organic synthesis.

InChI:InChI=1/C10H10N2O5/c1-2-17-10(14)9(13)11-7-3-5-8(6-4-7)12(15)16/h3-6H,2H2,1H3,(H,11,13)

Upstream product

• 2009-97-4 ethyl 2-diazo-3-oxobutanoate 
• 100-01-6 4-nitro-aniline 
• 1457-85-8 Ethyl oxanilate 
• 7697-37-2 nitric acid 
• 64-17-5 ethanol 
• 4755-77-5 Ethyl oxalyl chloride 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 57864-89-8 1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazine-3-carboxylic acid 4-nitro-anilide 
• 64-17-5 ethanol 
• 144-62-7 oxalic acid 
• 100-01-6 4-nitro-aniline 
• 72304-33-7 N-(5-amino-[1,3,4]thiadiazole-2-sulfonyl)-N'-(4-nitro-phenyl)-oxalamide 
• 17794-28-4 ethyl 2-((4-aminophenyl)amino)-2-oxoacetate 
• 830347-96-1 C₂₁H₂₅N₃O₉ 
• 1029803-83-5 N-(4,6-dimethylpyridin-2-yl)-N'-(4-nitrophenyl)oxalamide 
• 53117-74-1 (4-nitro-phenyl)-oxalamic acid isopropylidenehydrazide 

Relevant articles and documents

New N-phenyl-4,5-dibromopyrrolamides and N-Phenylindolamides as ATPase inhibitors of DNA gyrase

Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 μM against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds - especially by varying their size, the position and orientation of key functional groups, and their acid-base properties. The structure-activity relationship (SAR) was examined and the results were rationalised with molecular docking.

New Highlights in the Synthesis of 4-Aryl-1,4-dihydropyrazines

The 4-aryl-1,4-dihydropyrazines were prepared via the cyclization of N,N-bisalkylated anilines with ammonium acetate. These reactions were aided by improvements in the synthesis of N,N-bisalkylated anilines which were alkylated with anilines using ethyl 2-diazo acetoacetate in a reaction catalyzed by rhodium acetate in the absence of oxygen. A possible mechanistic route is postulated on the basis of the isolation of the N-alkylation intermediates, which were determined to be N-aryloxamates by 1H NMR data and X-ray diffraction.

Synthesis of unsymmetrical pyrrolo[3,2-b]pyrrole-2,5-diones and bis(quinazolin-4-on-2-yls) by double-anion-capture reactions of unsymmetrical oxaldi(arylimidoyl) dichlorides

Unsymmetrical pyrrolo[3,2-b]pyrrole-2,5-diones and bis(quinazolin-4-on-2- yls) were prepared by one-pot cyclisations of unsymmetrical oxaldi(arylimidoyl) dichlorides. Georg Thieme Verlag Stuttgart.