Amifloxacin

Base Information

• Chemical Name: Amifloxacin
• CAS No.: 86393-37-5
• Molecular Formula: C16H19 F N4 O3
• Molecular Weight: 334.35
• European Community (EC) Number: 289-231-8
• UNII: 5TU5227KYQ
• DSSTox Substance ID: DTXSID20235519
• Nikkaji Number: J23.319F
• Wikipedia: Amifloxacin
• Wikidata: Q4746186
• NCI Thesaurus Code: C72696
• Metabolomics Workbench ID: 49564
• ChEMBL ID: CHEMBL6231
• Mol file: 86393-37-5.mol

Synonyms:6-fluoro-1-methylamino-7-(4-methylpiperazin-1-yl)-1,4-dihydroquinolin-4-one-3-carboxylic acid;amifloxacin;Win 49375;Win-49375

Chemical Property of Amifloxacin

Chemical Property:

• Vapor Pressure: 3.61E-12mmHg at 25°C
• Melting Point: 300 °C (decomp)
• Boiling Point: 532.5°Cat760mmHg
• PKA: 6.17±0.41(Predicted)
• Flash Point: 275.8°C
• PSA: 77.81000
• Density: 1.44g/cm³
• LogP: 0.83980
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 334.14411864
• Heavy Atom Count: 24
• Complexity: 547

Purity/Quality:

98%Min ^*data from raw suppliers

AMIFLOXACIN 95.00% ^*data from reagent 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)N3CCN(CC3)C)F)C(=O)O
• Uses: Antibacterial.

Technology Process of Amifloxacin

There total 11 articles about Amifloxacin 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: 65.0%

1-methyl-piperazine (109-01-3) + 6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (88569-39-5) → amifloxacin (86393-37-5)

Guidance literature:

In pyridine; for 15h; Heating;

DOI:10.1021/jm00375a003

Reference yield:

ethyl 1-(N-formyl-N-methyl)amino-6-fluoro-7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylate (88569-34-0) → amifloxacin (86393-37-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaOH / H₂O / 2 h / Heating

2: 65 percent / pyridine / 15 h / Heating

With sodium hydroxide; In pyridine; water;

DOI:10.1021/jm00375a003

Reference yield:

ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline 3-carboxylate (75073-15-3) → amifloxacin (86393-37-5)

Guidance literature:

Multi-step reaction with 5 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

5: 65 percent / pyridine / 15 h / Heating

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

DOI:10.1021/jm00375a003

upstream raw materials:

1-methyl-piperazine

6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

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

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

Downstream raw materials:

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

Refernces

• 1、 Hermecz, Istvan,Vasvari-Debreczy, Lelle,Podanyi, Benjamin,Kereszturi, Geza,Balogh, Maria,Horvath, Agnes,Varkonyi, Peter. "Regioselective nucleophilic substitution of halogen derivatives of 1-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids". . p. 1111 - 1116. Retrieved 2007/10/03.
• 2、 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.