104599-90-8

Basic information

• Product Name: 3-Quinolinecarboxylic acid, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-, Methyl ester
• Synonyms: 3-Quinolinecarboxylic acid, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-, Methyl ester
• CAS NO: 104599-90-8
• Molecular Formula: C₁₄H₁₁ClFNO₃
• Molecular Weight: 295.6934432
• Mol File: 104599-90-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 441.2°C at 760 mmHg
• Flash Point: 220.6°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 5.55E-08mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: 3-Quinolinecarboxylic acid, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolinecarboxylic acid, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-, Methyl ester(104599-90-8)
• EPA Substance Registry System: 3-Quinolinecarboxylic acid, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-, Methyl ester(104599-90-8)

Safety Data

• Hazardous Substances Data: 104599-90-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H11ClFNO3/c1-20-14(19)9-6-17(7-2-3-7)12-5-10(15)11(16)4-8(12)13(9)18/h4-7H,2-3H2,1H3

Upstream product

• 67-56-1 methanol 
• 86393-33-1 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 
• 74-88-4 methyl iodide 
• 72396-25-9 N-(Cyclopropylamino)acrylsaeure-methylester 
• 86393-34-2 2,4-dichloro-5-fluorobenzoyl chloride 
• 704-10-9 2,4-dichloro-5-fluoroacetophenone 
• 104600-21-7 methyl 3-cyclopropylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylate 
• 105392-26-5 3-Cyclopropylamino-2-(2,4-dichlor-5-fluorbenzoyl)acrylsaeure-methylester 

Downstream Products

• 93106-60-6 enrofloxacin 
• 93107-08-5 ciprofloxacin hydrochloride 

Relevant articles and documents

Dual role of Rh(III) catalyst enables regioselective halogenation of (electron-rich) heterocycles

The Rh(III)-catalyzed selective bromination and iodination of electron-rich heterocycles is reported. Kinetic investigations show that Rh plays a dual role in the bromination, catalyzing the directed halogenation and preventing the inherent halogenation of these substrates. As a result, this method gives highly selective access to valuable halogenated heterocycles with regiochemistry complementary to those obtained using uncatalyzed approaches, which rely on the inherent reactivity of these classes of substrates. Furans, thiophenes, benzothiophenes, pyrazoles, quinolones, and chromones can be applied.

Molecular structures of new ciprofloxacin derivatives

Two new derivatives from the ciprofloxacin fluoroquinoline family, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo- quinoline-3-methylcarbamate and 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-(3-oxopyrazolo) [4,3-c]quinoline, were synthesised, tested for antibacterial activity and crystallised. Their molecular and crystal structures were determined. Tests in vitro reveal lower activities than for ciprofloxacin. Characteristic structural features of these compounds are comparable to data for other known fluoroquinolines. The bicyclic quinoline ring is planar in both compounds; the carbamate side chain and five-membered pyrazolo ring are almost coplanar with it. A piperazinyl ring exhibits a chair conformation. In the crystal packing of the carbamate analogue, two C-HO interactions form a dimer. The pyrazolo derivative crystallises as solvate with 1.5 water molecules per quinoline molecule. In its crystal structure donor and acceptor functionalities form dimers, via hydrogen bonds, which are connected into an infinite pattern through hydrogen bonded water molecules.

Cycloaracylation of Enamines, I. - Synthesis of 4-Quinolone-3-carboxylic Acids

Starting with o-halobenzoyl chlorides 4 and open-chain secondary enamines 5, a new synthesis of 4-quinolone-3-carboxylic acids 12 is described.The reaction of 7-haloquinolone-3-carboxylic acids 12a-k with aliphatic amines 14 produces highly active antibacterial 7-aminoquinolone-3-carboxylic acids 15.The main product of the 1-cyclopropyl series, "ciprofloxacin" (15a), is being developed as a broad-spectrum chemotherapeutic agent.