7-Chloro-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Base Information

• Chemical Name: 7-Chloro-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 98105-79-4
• Molecular Formula: C16H8 Cl F2 N O3
• Molecular Weight: 335.694
• Hs Code.: 2933499090
• UNII: Y7D63U5WUG
• DSSTox Substance ID: DTXSID90275624
• Nikkaji Number: J811.636I
• Wikidata: Q72450780
• ChEMBL ID: CHEMBL1472251
• Mol file: 98105-79-4.mol

Synonyms:98105-79-4;7-Chloro-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid;7-chloro-6-fluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid;Y7D63U5WUG;7-Chloro-6-fluoro-1-(4'-fluoro phenyl)-1,4-dihydro-4-oxo-3-quinoline carboxylic acid;3-Quinolinecarboxylic acid, 7-chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-;7-chloro-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid;C16H8ClF2NO3;Difloxacin Impurity G;UNII-Y7D63U5WUG;AQ-405/42300515;MLS001180944;SCHEMBL8094811;CHEMBL1472251;DTXSID90275624;HMS2817F19;KUC103470N;AMY40422;MFCD04153757;7-chloro-6-fluoro-1-(4-fluorophenyl)-4-oxo-quinoline-3-carboxylic acid;AKOS000282596;AC-8365;SB73038;7-Chloro-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylicacid;NCGC00247250-01;DS-16791;SMR000477830;FT-0653189;C77354;A845809;BRD-K49134924-001-06-5;1-(p-fluoro-phenyl-6-fluoro-7-chloro-4-oxo-3-quinolinecarboxylic acid;7-chloro-6-fluoro-1-(4-fluorophenyl)-4-oxo-3-quinolinecarboxylic acid;1-(4-Fluorophenyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;7-chloranyl-6-fluoranyl-1-(4-fluorophenyl)-4-oxidanylidene-quinoline-3-carboxylic acid;7-chloro-1-p-fluorophenyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

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

Chemical Property:

• Melting Point: 260-264℃
• Boiling Point: 513.8°Cat760mmHg
• Flash Point: 264.5°C
• PSA: 59.30000
• Density: 1.584g/cm³
• LogP: 3.62050
• Storage Temp.: 2-8°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 335.0160771
• Heavy Atom Count: 23
• Complexity: 533

Purity/Quality:

99% ^*data from raw suppliers

7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1N2C=C(C(=O)C3=CC(=C(C=C32)Cl)F)C(=O)O)F
• Uses: 7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid is a 1-arylated derivative of 1,4-dihydro-4-oxoquinoline-3-carboxylic acid with antibacterial activity.

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

There total 11 articles about 7-Chloro-6-fluoro-1-(4-fluorophenyl)-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: 54.0%

1-(4-Aminophenyl)-7-chloro-6-fluoro-4-oxoquinoline-3-carboxylic Acid (126362-90-1) → 7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (98105-79-4)

Guidance literature:

With hydrogen fluoride; sodium nitrite; In pyridine; a) Dissolving in HF and pyridine at 0 deg C and then 30 min at room temperature b) Sodium nitrite was added at 0 deg C c) Then 30 min at 30 deg C and 3h at 70 deg C;

Reference yield:

1-(4'-fluoro-phenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester (98105-80-7) → 7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (98105-79-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 80 ℃; for 1.5h; Yield given;

DOI:10.1021/jm00149a003

Reference yield:

2,4-dichloro-5-fluoroacetophenone (704-10-9) → 7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (98105-79-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / NaH / 1.5 h / 80 °C

2: Ac₂O / 2 h / 130 °C

3: CH₂Cl₂ / 0.5 h / Ambient temperature

4: NaH / 1,2-dimethoxy-ethane / 3 h / 80 °C

5: aq. NaOH / tetrahydrofuran / 1.5 h / 80 °C

With sodium hydroxide; acetic anhydride; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/jm00149a003

upstream raw materials:

1-(4-Aminophenyl)-7-chloro-6-fluoro-4-oxoquinoline-3-carboxylic Acid

1-(4'-fluoro-phenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester

2,4-dichloro-5-fluoroacetophenone

ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate

Downstream raw materials:

6-Fluoro-1-(4-fluoro-phenyl)-7-(3-hydroxy-pyrrolidin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

6-Fluoro-1-(4-fluoro-phenyl)-7-morpholin-4-yl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

6-Fluoro-1-(4-fluoro-phenyl)-4-oxo-7-thiomorpholin-4-yl-1,4-dihydro-quinoline-3-carboxylic acid

6-Fluoro-1-(4-fluoro-phenyl)-4-oxo-7-(3-oxo-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid

Refernces

• 1、 -. "7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids". . . Retrieved 2008/06/13.
• 2、 -. "Quinoline antibacterial compounds". . . Retrieved 2008/06/13.