21617-16-3

Basic information

• Product Name: 5-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE
• Synonyms: 5-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE;5-CHLORO-1,2,3,4-TETRAHYDROQUINOLIN-4-ONE
• CAS NO: 21617-16-3
• Molecular Formula: C₉H₈ClNO
• Molecular Weight: 181.62
• Mol File: 21617-16-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE(21617-16-3)
• EPA Substance Registry System: 5-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE(21617-16-3)

Safety Data

• Hazardous Substances Data: 21617-16-3(Hazardous Substances Data)

Upstream product

• 625-99-0 3-iodochlorobenzene 
• 76227-98-0 1-(3-chlorophenyl)-azetidin-2-one 
• 66737-56-2 N-(3-chlorophenyl)-N-<(4-methylphenyl)sulfonyl>-β-alanine 

Relevant articles and documents

Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2- ones

N-Arylazetidin-2-ones of the general form 1, which are readily prepared by GoldbergBuchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 018°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).

Structure-activity relationships of antimalarial indoloquinolines

Structure-activity relationships have been ascertained and chemical metodology developed for a series of antimalarial 3-chloroindoloquinoline-5-oxides.The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3.Substitution at positions 7,8,9,10 in not essential, although the most potent analog in our studies was the 8-nitro compound 4vv. indoloquinolines / antimalarial agents

Formation of 2,3-Dihydro-4(1H)-quinolones and Related Compounds via Fries-type Acid-catalysed Rearrangement of 1-Arylazetidin-2-ones

A variety of 1-arylazetidin-2-ones were treated with trifluoroacetic acid under reflux, methanesulphonic acid at 100 deg C, or conc. sulphuric acid to give the corresponding 2,3-dihydro-4(1H)-quinolones via acyl migration and N-CO fission.In the case of 1-(3-substituted phenyl)azetidin-2-ones, two positional isomeric products, 5- and 7-substituted 2,3-dihydro-4(1H)-quinolones were obtained. 4-Methyl, 4-ethoxycarbonyl, and 4-piperidin-2-yl-1-arylazetidin-2-ones and their analogues were also converted into the corresponding 2-substituted 2,3-dihydro-4(1H)-quinolones under acidic conditions.The 3-substituted 1-phenylazetidin-2-ones (36) and (37) were converted into the furoquinoline systems (38) and (40), respectively, by application of this method.