58013-72-2

Basic information

• Product Name: 3-benzyl-3-chloro-2,4(1H,3H)-quinolinedione
• Synonyms: 3-benzyl-3-chloro-2,4(1H,3H)-quinolinedione
• CAS NO: 58013-72-2
• Molecular Formula: C₁₆H₁₂ClNO₂
• Molecular Weight: 285.72498
• Mol File: 58013-72-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 490.1°C at 760 mmHg
• Flash Point: 250.2°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 9.45E-10mmHg at 25°C
• Refractive Index: 1.649
• CAS DataBase Reference: 3-benzyl-3-chloro-2,4(1H,3H)-quinolinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzyl-3-chloro-2,4(1H,3H)-quinolinedione(58013-72-2)
• EPA Substance Registry System: 3-benzyl-3-chloro-2,4(1H,3H)-quinolinedione(58013-72-2)

Safety Data

• Hazardous Substances Data: 58013-72-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12ClNO2/c17-16(10-11-6-2-1-3-7-11)14(19)12-8-4-5-9-13(12)18-15(16)20/h1-9H,10H2,(H,18,20)/t16-/m1/s1

Upstream product

• 15000-41-6 3-benzyl-4-hydroxy-2-quinolone 
• 144603-93-0 3-azido-3-benzylquinoline-2,4(1H,3H)-dione 

Downstream Products

• 58013-70-0 1-(3-Benzyl-2,4-dioxo-1,2,3,4-tetrahydrochinolin-3-yl)-pyridinium-chlorid 
• 144603-57-6 3-Benzyl-3-fluoro-1H-quinoline-2,4-dione 
• 144603-93-0 3-azido-3-benzylquinoline-2,4(1H,3H)-dione 
• 84261-47-2 3-benzyl-3-hydroxyquinoline-2,4(1H,3H)-dione 
• 146765-17-5 3-amino-3-benzylquinoline-2,4(1H,3H)-dione 
• 477949-99-8 3-benzyl-3-butylaminoquinoline-2,4-(1H,3H)-dione 
• 477950-01-9 3-benzyl-3-benzylaminoquinoline-2,4-(1H,3H)-dione 
• 15000-41-6 3-benzyl-4-hydroxy-2-quinolone 
• 92859-63-7 3-benzyl-3-bromoquinoline-2,4(1H,3H)-dione 

Relevant articles and documents

Stereochemistry of the reduction of α-chloroketones with sodium borohydride—application to 3-chloroquinoline-2,4-diones: Dedicated to the memory of Professor Dr.?Vojeslav ?těrba who died in September 2015 being nearly 93 years old

3-Chloroquinoline-2,4-diones were reduced with sodium borohydride to give syn- and anti-chlorohydrins, the stereochemistry of which was established by NMR spectroscopy. Both stereoisomeric chlorohydrins were reacted with potassium carbonate in methanol. a

Syntheses of 3-aminoquinoline-2,4(1H,3H)-diones

Reaction of 3-chloro- (2) and 3-bromoquinoline-2,4(1H,3H)-diones (3) with excess of primary alkyl- or arylamines in dimethylformamide provides the corresponding 3-alkyl- or 3-arylamino derivatives (4). Compounds (4) with the primary amino group at the 3 position were best prepared by reaction of 2 with in situ generated ammonia under anhydrous conditions. An alternative approach to the primary amines (4) via reduction of 3-azidoquinoline-2,4(1H,3H)-diones (5) was investigated. The reduction of 5 with zinc in acetic acid gave moderate to good yields of the desired products, while the reaction with triphenylphosphine afforded exclusively 4-hydroxyquinolin-2(1H)-one (1).