84261-53-0

Basic information

• Product Name: 3-ethyl-3-hydroxy-1-phenylquinoline-2,4(1H,3H)-dione
• Synonyms: 3-Ethyl-3-hydroxy-1-phenyl-2,4(1H,3H)-quinolinedione
• CAS NO: 84261-53-0
• Molecular Formula: C₁₇H₁₅NO₃
• Molecular Weight: 281.3059
• Mol File: 84261-53-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 550.3°C at 760 mmHg
• Flash Point: 286.6°C
• Density: 1.293g/cm³
• Vapor Pressure: 6.04E-13mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: 3-ethyl-3-hydroxy-1-phenylquinoline-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ethyl-3-hydroxy-1-phenylquinoline-2,4(1H,3H)-dione(84261-53-0)
• EPA Substance Registry System: 3-ethyl-3-hydroxy-1-phenylquinoline-2,4(1H,3H)-dione(84261-53-0)

Safety Data

• Hazardous Substances Data: 84261-53-0(Hazardous Substances Data)

Upstream product

• 1399323-95-5 3-ethyl-1,2,3,4-tetrahydro-2,4-dioxo-1-phenylquinolin-3-yl thiocyanate 
• 133-13-1 ethyl diethyl malonate 
• 84261-43-8 3-ethyl-4-hydroxy-1-phenylquinolin-2(1H)-one 

Relevant articles and documents

Modified riemschneider reaction of 3-thiocyanatoquinolinediones

The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H2SO4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly [1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds. Copyright

Novel ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones in aqueous alkali. The first convenient route to 2-hydroxyindoxyls

Ring contraction of 3-hydroxy-2,4(1H, 3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.