7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Base Information

• Chemical Name: 7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• CAS No.: 100492-04-4
• Molecular Formula: C15H6 Cl F3 N2 O3
• Molecular Weight: 354.672
• European Community (EC) Number: 917-532-2
• DSSTox Substance ID: DTXSID00441595
• Nikkaji Number: J243.075D
• Mol file: 100492-04-4.mol

Synonyms:100492-04-4;7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic Acid;1,8-Naphthyridine-3-carboxylic acid, 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-;1-(2,4-DIFLUOROPHENYL)-6-1LUORO-7-CHLONDE-4-OXO-1,4-DIHYDRO-1,8-NAPTHYRIDINE-3-CARBOXYLIC ACID[TOSUF;1-(2,4-DIFLUOROPHENYL)-6-1LUORO-7-CHLONDE-4-OXO-1,4-DIHYDRO-1,8-NAPTHYRIDINE-3-CARBOXYLIC ACID[TOSUFLOXACIN PHARMACEUTICAL INTERMEDIATE];WTCJJEJMYYASNT-UHFFFAOYSA-N;SCHEMBL501152;DTXSID00441595;AKOS015896863;AT37722;7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro 4-oxo-1,8-naphthyridine-3-carboxylic acid;3-CHLORO-2,2-DIMETHYLPROPIONICACID;A16208;7-Chloro-1(2,4-Difluorophenyl-1,4-Dihydro)-6-Dluor;7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid;1-( 2,4-Difluorophenyl)-6-fluoro-7-chloro-4-Oxo-1,4-dihydro-1,8-napthyridine-3-carboxylic Acid;1-(2,4-difluorophenyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid;7-chloro-6-fluoro-1-(2,4-difluoro-phenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-chloro-6-fluoro-1-(2,4-difluorophenyl) 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-chloro-6-fluoro-1-{2,4-difluoro-phenyl) -1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Chemical Property of 7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Chemical Property:

• PSA: 72.19000
• LogP: 3.15460
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 354.0019042
• Heavy Atom Count: 24
• Complexity: 576

Purity/Quality:

≥99.0% ^*data from raw suppliers

7-CHLORO-1-(2,4-DIFLUOROPHENYL)-6-FLUORO-4-OXO-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1F)F)N2C=C(C(=O)C3=CC(=C(N=C32)Cl)F)C(=O)O

Technology Process of 7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

There total 7 articles about 7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-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: 97.1%

ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (100491-29-0) → 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (100492-04-4)

Guidance literature:

In hydrogenchloride; water;

Reference yield:

2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid (82671-06-5) → 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (100492-04-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: thionyl chloride / 2.5 h / 85 °C

2.1: 2,2'-biquinoline; n-butyllithium / tetrahydrofuran; hexane / 1 h / -50 - 20 °C

3.1: acetic anhydride / 1 h / 130 °C

3.2: 1 h

4.1: sodium hydride / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux

5.1: acetic acid; hydrogenchloride / 7.5 h / Reflux

With hydrogenchloride; n-butyllithium; thionyl chloride; 2,2'-biquinoline; sodium hydride; acetic acid; In tetrahydrofuran; hexane; acetic anhydride;

Reference yield:

ethyl-3,1-(2,4-difluoroanilino)-2-(2,6-dichloro-5-fluoronicotinyl) acrylate (100490-99-1) → 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (100492-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux

2: acetic acid; hydrogenchloride / 7.5 h / Reflux

With hydrogenchloride; sodium hydride; acetic acid; In tetrahydrofuran;

upstream raw materials:

ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate

ethyl-3,1-(2,4-difluoroanilino)-2-(2,6-dichloro-5-fluoronicotinyl) acrylate

ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate

Downstream raw materials:

trovafloxacin

C₂₃H₂₁F₃N₆O₅

C₂₂H₂₀F₃N₅O₄

Refernces

• 1、 -. "ANTIVIRAL AND ANTIMICROBIAL COMPOUNDS". Paragraph 0128; 0134. . Retrieved 2014/03/25.
• 2、 -. "Process for preparing quinolone and naphthyridone carboxylic acids". . . Retrieved 2008/06/13.