7-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid

Base Information

• Chemical Name: 7-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid
• CAS No.: 88569-39-5
• Molecular Formula: C11H8 Cl F N2 O3
• Molecular Weight: 270.648
• European Community (EC) Number: 289-428-9
• UNII: HZ5TR7G8NN
• DSSTox Substance ID: DTXSID30237125
• Nikkaji Number: J348.551J
• Mol file: 88569-39-5.mol

Synonyms:88569-39-5;7-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid;7-chloro-6-fluoro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid;EINECS 289-428-9;7-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxo-3-quinolinecarboxylic acid;7-Chloro-6-fluoro-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;HZ5TR7G8NN;SCHEMBL6212035;DTXSID30237125;RCNJBEXSAWUACU-UHFFFAOYSA-N;C11-H8-Cl-F-N2-O3;AKOS000279180;3-Quinolinecarboxylic acid, 7-chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxo-;6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid;7-chloro-6-fluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid

Chemical Property of 7-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.26E-08mmHg at 25°C
• Boiling Point: 443°C at 760 mmHg
• Flash Point: 221.7°C
• PSA: 71.33000
• Density: 1.61g/cm³
• LogP: 1.73850
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 270.0207480
• Heavy Atom Count: 18
• Complexity: 415

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNN1C=C(C(=O)C2=CC(=C(C=C21)Cl)F)C(=O)O

Technology Process of 7-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid

There total 10 articles about 7-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxoquinoline-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: 94.0%

ethyl 1-(N-formyl-N-methyl)amino-6-fluoro-7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylate (88569-34-0) → 6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (88569-39-5)

Guidance literature:

With hydrogenchloride; In acetonitrile; at 90 ℃; for 7h;

DOI:10.1002/jhet.5570220421

Reference yield:

ethyl 7-chloro-6-fluoro-1-[formyl(2-propenyl)amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylate (88569-38-4) → 6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (88569-39-5) + 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-(2-propenylamino)-3-quinolinecarboxylic acid (88569-44-2)

Guidance literature:

With sodium hydroxide;

Reference yield:

ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline 3-carboxylate (75073-15-3) → 6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (88569-39-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / K₂CO₃, O-(2,4-dinitrophenyl)hydroxylamine / dimethylformamide / 3 h / Ambient temperature

2: 1.) acetic anhydride / 1.) 0-50 deg C, 30 min, 2.) 25 deg C, 3.5 d

3: 90 percent / K₂CO₃ / dimethylformamide / 1.5 h / Ambient temperature

4: 91 percent / NaOH / H₂O / 2 h / Heating

With sodium hydroxide; acetic anhydride; potassium carbonate; O-(2,4-dinitrophenyl)hydroxylamine; In water; N,N-dimethyl-formamide;

DOI:10.1021/jm00375a003

upstream raw materials:

ethyl 1-(N-formyl-N-methyl)amino-6-fluoro-7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylate

ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline 3-carboxylate

ethyl 1-amino-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

ethyl 7-chloro-6-fluoro-1-(formylamino)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Downstream raw materials:

toluene-4-sulfonic acid

6-fluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid 4'-oxide

amifloxacin

A 56559

Refernces

• 1、 Chu. "A regiospecific synthesis of 1-methylamino-6-fluoro-7-(4-methylpiperazin-1-yl)-1,4-dihydro-4-oxoquinoli ne-3-carboxylic acid". . p. 1033 - 1034. Retrieved 2007/10/02.
• 2、 Wentland,Bailey,Cornett,Dobson,Powles,Wagner. "Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: Synthesis and structure-activity relationships". . p. 1103 - 1108. Retrieved 2007/10/02.