144603-33-8

Basic information

• Product Name: 3-chloro-1-methyl-3-phenyl-2,4(1H,3H)-quinolinedione
• Synonyms: 3-chloro-1-methyl-3-phenyl-2,4(1H,3H)-quinolinedione
• CAS NO: 144603-33-8
• Molecular Formula: C₁₆H₁₂ClNO₂
• Molecular Weight: 285.72498
• Mol File: 144603-33-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-chloro-1-methyl-3-phenyl-2,4(1H,3H)-quinolinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-1-methyl-3-phenyl-2,4(1H,3H)-quinolinedione(144603-33-8)
• EPA Substance Registry System: 3-chloro-1-methyl-3-phenyl-2,4(1H,3H)-quinolinedione(144603-33-8)

Safety Data

• Hazardous Substances Data: 144603-33-8(Hazardous Substances Data)

Upstream product

• 519-66-4 4-hydroxy-1-methyl-3-phenylquinolin-2-one 

Downstream Products

• 113737-84-1 3-hydroxy-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 1432733-33-9 3-(2,5-dimethylphenylamino)-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 519-66-4 4-hydroxy-1-methyl-3-phenylquinolin-2-one 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 1432733-39-5 1,2-dihydro-1-methyl-2-oxo-3-phenylquinolin-4-yl dihydrogen phosphate hydrate 
• 56857-90-0 4-Chloro-1-methyl-2-oxo-3-phenyl-1,2-dihydroquinoline 
• 108832-15-1 2,4-dichloro-3-phenylquinoline 
• 521980-39-2 1-methyl-3-phenyl-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanate 
• 22462-93-7 4-acetyoxy-1-methyl-3-phenyl-1H-quinolin-2-one 
• 477950-10-0 3-butylamino-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 477950-08-6 3-amino-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 477950-11-1 3-cyclohexylamino-1-methyl-3-phenylquinoline-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

Reaction of some 2-quinolone derivatives with phosphoryl chloride: Synthesis of novel phosphoric acid esters of 4-hydroxy-2-quinolone

3-Chloroquinoline-2,4-diones do not react with phosphoryl chloride, however, 2,4-dichloroquinolines and/or 4-chloroquinolin-2-ones are formed in the presence of N,N-dimethylaniline. Along with these compounds, small quantities of novel dihydrogen phosphates of 4-hydroxyquinolin-2-ones were isolated. We outline a simple procedure that allows for the preparation of these compounds in moderate to good yields. All compounds were characterized by 1H and 13C NMR, IR, EI-MS, and ESI-MS spectroscopy, and in select cases by 31P NMR spectroscopy.

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).

Halogenation Reactions in Position 3 of Quinoline-2,4-dione Systems by Electrophilic Substitution and Halogen Exchange

3-Substituted 4-hydroxy-2(1H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10.Reactions of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11.Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13.Similarly the dichloro quinolinediones 10an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.Keywords.Fluorination; 4-Hydroxy-2(1H)-quinolones, 3-alkyl/3-aryl/3-fluoro; 1-Hydroxy-benzoquinolizine-3-ones, 2-alkyl/3-aryl; Quinoline-2,4(1H,3H)-diones, 3-azido-3-alkyl/3-aryl, 3-bromo-3-alkyl/3-aryl, 3-chloro-3-alkyl/3-aryl, 3-fluoro-3-alkyl/3-aryl, 3-dichloromethyl-3-alkyl/3-aryl, 3-chloro-3-fluoro.