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
• Uses: Norfloxacin intermediate. 7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid (Norfloxacin EP Impurity A) is a Norfloxacin intermediate. Norfloxacin EP Impurity A; Norfloxacin USP Related Compound A (7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid).

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-7-<3-(cyanomethyl)-4-benzyl-1-piperazinyl>-1,4-dihydro-4-oxo-3-quinolinecaboxylic acid

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

N-acetylnorfloxacin

Refernces

• 1、 Rameshkumar, Natesh,Ashokkumar, Mohan,Subramanian, Ekambaram Harihara,Ilavarasan, Raju,Sridhar, Seshaiah Krishnan. "Synthesis of 6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives as potential antimicrobial agents". . p. 1001 - 1004. Retrieved 2003.
• 2、 -. "Chemical synthesis method for norfloxacin". Paragraph 0016. . Retrieved 2018/04/01.
• 3、 Azad, Chandra S.,Narula, Anudeep K.. "An operational transformation of 3-carboxy-4-quinolones into 3-nitro-4-quinolones via ipso-nitration using polysaccharide supported copper nanoparticles: Synthesis of 3-tetrazolyl bioisosteres of 3-carboxy-4-quinolones as antibacterial agents". . p. 19052 - 19059. Retrieved 2016/03/01.