Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Base Information

• Chemical Name: Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
• CAS No.: 96568-07-9
• Molecular Formula: C14H12ClFN2O3
• Molecular Weight: 310.712
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30471143
• Nikkaji Number: J385.980K
• Wikidata: Q72474105
• Mol file: 96568-07-9.mol

Synonyms:96568-07-9;Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;Ethyl 1-Cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthylridine carboxylate;Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate;7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester;MFCD08458313;ethyl 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate;C14H12ClFN2O3;SCHEMBL5422476;DTXSID30471143;RWCZOVMOKFTUAD-UHFFFAOYSA-N;AKOS015999949;AC-7741;AS-13782;SY047866;CS-0046189;FT-0651675;ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate;Ethyl7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;1-cyclopropyl-6-fluoro-7- chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester;1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4- oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester;cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester;Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-2-carboxylate

Chemical Property of Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.692
• Boiling Point: 464.205 °C at 760 mmHg
• Flash Point: 234.543 °C
• PSA: 61.19000
• Density: 1.512 g/cm³
• LogP: 2.70060
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 310.0520481
• Heavy Atom Count: 21
• Complexity: 495

Purity/Quality:

98.0%Min ^*data from raw suppliers

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN(C2=NC(=C(C=C2C1=O)F)Cl)C3CC3
• Uses: 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid Ethyl Ester is a fluoroquinolone derivative used in the preparation of antibacterial agents.

Technology Process of Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

There total 1 articles about Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-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:

2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid (82671-06-5) → ethyl-7-chloro-6-fluoro-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (96568-07-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA / 1.) THF, hexane, -73 deg C, 3 h, 2.) THF, hexane, from -66 deg C, 1 h

2: 19.7 g / oxalyl dichloride, DMF / CH₂Cl₂ / 5 h / 25 °C

3: 1.) BuLi / 1.) THF, hexane, -25 deg C, 30 min, 2.) THF, hexane, -70 deg C, 1.5 h

4: 30.6 g / acetic anhydride / 120 °C

5: ethanol / 2 h / Ambient temperature

6: 20 percent / NaH / dioxane / 1.5 h / 45 °C

With n-butyllithium; oxalyl dichloride; acetic anhydride; sodium hydride; N,N-dimethyl-formamide; lithium diisopropyl amide; In 1,4-dioxane; ethanol; dichloromethane;

DOI:10.1002/jhet.5570290453

Reference yield: 78.0%

ethyl-7-chloro-6-fluoro-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (96568-07-9) → 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid (100361-18-0)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; for 2h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.02.019

Reference yield: 76.0%

1,1-dimethylethyl-<3-(tri-n-butylstannyl)-2-cyclohexen-1-yl>carbamate (129081-78-3) + ethyl-7-chloro-6-fluoro-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (96568-07-9) → ethyl 1-cyclopropyl-7-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-1-cyclohexen-1-yl>-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (129081-81-8)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; roomtemp. to 100 deg C, 111 h;

DOI:10.1002/jhet.5570280133

upstream raw materials:

2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid

Downstream raw materials:

ethyl 1-cyclopropyl-7-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-1-cyclohexen-1-yl>-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,2,3,4-tetrahydro-4-oxo-1,8-naphthyridine-3-carboxylate

7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

ciprofloxacin

Refernces

• 1、 Bouzard, D.,Cesare, P. Di,Essiz, M.,Jacquet, J. P.,Ledoussal, B.,et al.. "Fluoronaphthyridines as Antibacterial Agents. 4. Synthesis and Structure-Activity Relationships of 5-Substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acids". . p. 518 - 525. Retrieved 2007/10/02.