7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Base Information

• Chemical Name: 7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 68077-26-9
• Molecular Formula: C12H9 Cl F N O3
• Molecular Weight: 269.66
• Hs Code.: 2933499090
• European Community (EC) Number: 614-262-4
• UNII: 831B5OC9PQ
• DSSTox Substance ID: DTXSID90333112
• Nikkaji Number: J94.731H
• Wikidata: Q72450094
• ChEMBL ID: CHEMBL29989
• Mol file: 68077-26-9.mol

Synonyms:68077-26-9;7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid;1-ETHYL-7-CHLORO-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID;7-chloro-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid;3-Quinolinecarboxylic acid, 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-;7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid;831B5OC9PQ;7-Chloro-1,4-dihydro-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acid;7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid, 90per cent;7-chloro-1-ethyl-6-fluoro-4-oxohydroquinoline-3-carboxylic acid;7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid;UNII-831B5OC9PQ;Norfloxacin impurity A [EP];CHEMBL29989;SCHEMBL3809668;DTXSID90333112;CGA-78039;MFCD00792459;AKOS000276677;DS-5240;SB71731;AM20061438;C2897;CS-0036496;FT-0621372;NORFLOXACIN IMPURITY A [EP IMPURITY];M-193324;1-Ethyl-1,4-dihydro-4-oxo-6-fluoro-7-chloroquinoline-3-carboxylic acid;1-ethyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid;1-ethyl-6-fluoro-7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid;1-ethyl-6-fluoro-7-chloro-4-oxo1,4-dihydro-quinoline-3-carboxylic acid;1-ethyl-7-chloro-1,4-dihydro-6-fluoro-4-oxoquinoline-3-carboxylic acid

Chemical Property of 7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.92E-08mmHg at 25°C
• Melting Point: 279-281ºC
• Boiling Point: 437.9 °C at 760 mmHg
• PKA: -0.21±0.20(Predicted)
• Flash Point: 218.7 °C
• PSA: 59.30000
• Density: 1.489 g/cm³
• LogP: 2.51210
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 269.0254990
• Heavy Atom Count: 18
• Complexity: 412

Purity/Quality:

99% ^*data from raw suppliers

7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylicAcid,90% ^*data from reagent suppliers

Safty Information:

• Statements: 52/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C=C(C(=O)C2=CC(=C(C=C21)Cl)F)C(=O)O
• General Description: 1-Ethyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid is a key intermediate in the synthesis of quinolone antibiotics, such as norfloxacin, and exhibits significant antibacterial activity. Derivatives of 1-ETHYL-7-CHLORO-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID, including those with substituted piperazine groups, have demonstrated potent in vitro antimicrobial effects against various bacterial strains, including *Staphylococcus aureus*, *Escherichia coli*, and *Klebsiella pneumoniae*, with some showing weak antifungal activity. 1-ETHYL-7-CHLORO-6-FLUORO-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID's in vivo efficacy against *E. coli* has also been confirmed, with ED₅₀ values ranging from 50 to 160 mg/kg. Its structural modifications, particularly at the 7-position, influence its antimicrobial potency.

Technology Process of 7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

There total 14 articles about 7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (70458-94-5) → 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (68077-26-9)

Guidance literature:

1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester; With water; sodium hydroxide; In ethanol; at 90 ℃; for 1.5h;

With hydrogenchloride; In ethanol; water; pH=2;

DOI:10.1021/jm900411s

Reference yield: 76.0%

3-chloro-4-fluoro-N-ethylformanilide + 2-(4-morpholinylcarbonyl)ethanoic acid methyl ester (149859-18-7) → 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (68077-26-9)

Guidance literature:

With trichlorophosphate; at 100 ℃;

DOI:10.1039/c39950001319

Reference yield: 60.0%

N-(3-Chlor-4-fluor-phenyl)-N-ethyl-aminomethylen-meldrumsaeure (136491-18-4) → 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (68077-26-9)

Guidance literature:

With aluminium trichloride; In chlorobenzene; at 80 ℃; for 0.0833333h;

upstream raw materials:

1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

N-(3-Chlor-4-fluor-phenyl)-N-ethyl-aminomethylen-meldrumsaeure

2-(4-morpholinylcarbonyl)ethanoic acid methyl ester

7-Chloro-6-fluoro-4-hydroxy-3-quinolinecarboxylic acid ethyl ester

Downstream raw materials:

Pefloxacin

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

AS 1842856

Norfloxacin hydrochloride