Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylate
• CAS No.: 86483-54-7
• Molecular Formula: C15H13 Cl F N O3
• Molecular Weight: 309.725
• DSSTox Substance ID: DTXSID20346992
• Nikkaji Number: J3.192.634C
• Wikidata: Q82120449
• Mol file: 86483-54-7.mol

Synonyms:86483-54-7;ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylate;7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER;SCHEMBL7889777;DTXSID20346992;LS-140031;1-Cyclopropyl-4-oxo-6-fluoro-7-chloro-1,4-dihydroquinoline-3-carboxylic acid ethyl ester;7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, ethyl ester;Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate #;Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate;Ethyl7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate;7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLICACIDETHYLESTER

Chemical Property of Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylate

Chemical Property:

• PSA: 48.30000
• LogP: 3.30560
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 309.0567991
• Heavy Atom Count: 21
• Complexity: 491

Purity/Quality:

99% ^*data from raw suppliers

7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)Cl)C3CC3
• Uses: Ethyl 7-Chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylate is a quinolone derivative that has been studied as a reagent in the preparation of anti-HIV agents

Technology Process of Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylate

There total 2 articles about Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylate 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: 86.0%

N,N-dimethylaminoacrylic acid ethyl ester (16173-58-3) + tri-n-butylammonium bromide (37026-85-0) + 2,4-dichloro-5-fluorobenzoyl chloride (86393-34-2) + Cyclopropylamine (765-30-0) → ethyl 1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate (86483-54-7)

Guidance literature:

With potassium carbonate; acetic acid; triethylamine; In water; chlorobenzene; isopropyl alcohol;

Reference yield:

2,4-dichloro-5-fluorobenzoyl chloride (86393-34-2) → ethyl 1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate (86483-54-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Mg/ethanol, CCl₄ / ethanol; toluene / 1.) 0 to -5 deg C, 2.) 12 h, room temperature

2: p-toluenesulfonic acid / H₂O / 5 h / Heating

3: acetic anhydride / 2 h / Heating

4: 92 percent / ethanol / 1 h / Ambient temperature

5: 90 percent / potassium carbonate / dimethylformamide / 2 h / 140 - 150 °C

With tetrachloromethane; ethanol; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; magnesium; In ethanol; water; N,N-dimethyl-formamide; toluene;

Reference yield: 93.0%

ethyl 1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate (86483-54-7) → 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (86393-33-1,178489-04-8)

Guidance literature:

With sulfuric acid; In water; for 1.5h; Heating;

upstream raw materials:

2,4-dichloro-5-fluorobenzoyl chloride

N,N-dimethylaminoacrylic acid ethyl ester

tri-n-butylammonium bromide

Cyclopropylamine

Downstream raw materials:

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

ciprofloxacin hydrochloride

ciprofloxacin

enrofloxacin