Ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate
• CAS No.: 112811-71-9
• Molecular Formula: C16H15F2NO4
• Molecular Weight: 323.296
• Hs Code.: 2933499090
• European Community (EC) Number: 620-302-1
• UNII: X3CH2A9DUL
• Nikkaji Number: J1.631.307F
• Mol file: 112811-71-9.mol

Synonyms:112811-71-9;1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester;ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate;1-Cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester;1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid ethyl ester;X3CH2A9DUL;Moxifloxacin Difluoro Methoxy Ethyl Ester;ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxoquinoline-3-carboxylate;MFCD05864419;ETHYL 1-CYCLOPROPYL-6,7-DIFLUORO-8-METHOXY-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLATE;3-Quinolinecarboxylic acid, 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-, ethyl ester;Gatifloxacin macrolid;UNII-X3CH2A9DUL;SCHEMBL1989474;AMY18320;BCP10385;WAA96341;AC-297;AKOS005064002;Ethyl 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate;(S,S)-Cyclohexane-1,2-dicarboxylic acid;AS-13131;Gatifloxacin Carboxyclic Acid Ethyl Ester;SY053109;CS-0151711;E1147;FT-0642751;J-504572;Ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate;ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylate;Ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate;Ethyl-6,7-difluoro-1-cyclopropyl-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate;ethyl1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate;1-Cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid ethyl ester;1-Cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester;1-Cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline3-carboxylic acid ethyl ester

Chemical Property of Ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

Chemical Property:

• Appearance/Colour: Pale yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 179-181 °C
• Refractive Index: 1.578
• Boiling Point: 459.695 °C at 760 mmHg
• PKA: -2.98±0.40(Predicted)
• Flash Point: 231.816 °C
• PSA: 57.53000
• Density: 1.415 g/cm³
• LogP: 2.79990
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 323.09691428
• Heavy Atom Count: 23
• Complexity: 534

Purity/Quality:

99% ^*data from raw suppliers

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN(C2=C(C(=C(C=C2C1=O)F)F)OC)C3CC3
• Uses: Gatifloxacin intermediate Gatifloxacin intermediate.

Technology Process of Ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

There total 28 articles about Ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-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: 82.0%

ethyl α(Z)-[(diethylamino)methylene]-2,4,5-trifluoro-3-methoxy-β-oxo-benzenepropanoate + Cyclopropylamine (765-30-0) → ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (112811-71-9)

Guidance literature:

ethyl α(Z)-[(diethylamino)methylene]-2,4,5-trifluoro-3-methoxy-β-oxo-benzenepropanoate; Cyclopropylamine; In diethyl ether; ethanol; at 20 ℃; for 3h;

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 5h;

Reference yield: 81.0%

ethyl 2-(3-methoxy-2,4,5-trifluorobenzoyl)-3-(cyclopropylamino)acrylate → ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (112811-71-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 18h;

DOI:10.1021/jm00022a013

Reference yield: 63.16%

N,N-dimethylaminoacrylic acid ethyl ester (16173-58-3) + Cyclopropylamine (765-30-0) + 2,4,5-trifluoro-3-methoxybenzoyl chloride (112811-66-2) → ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (112811-71-9)

Guidance literature:

N,N-dimethylaminoacrylic acid ethyl ester; 2,4,5-trifluoro-3-methoxybenzoyl chloride; With triethylamine; In ethyl acetate; at 60 - 80 ℃; for 3h;

Cyclopropylamine; With acetic acid; In ethyl acetate; for 0.5h; Temperature;

upstream raw materials:

ethyl 3-(cyclopropylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate

ethyl α(E)-[(diethylamino)methylene]-2,4,5-trifluoro-3-methoxy-β-oxo-benzenepropanoate

3-methoxy-2,4,5-trifluorobenzoic acid

2,4,5-trifluoro-3-methoxybenzoyl chloride

Downstream raw materials:

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid-O³,O⁴(bis(acyloxy-O)) borate

C₂₄H₃₀FN₃O₆

C₂₄H₂₉BF₃N₃O₆

Refernces

• 1、 -. "Gatifloxacin and synthesis method thereof". Paragraph 0061-0062; 0065-0066; 0069-0070. . Retrieved 2020/03/23.
• 2、 -. "Synthesis method of gatifloxacin cyclic ester". Paragraph 0032; 0039; 0044-0045; 0050-0051; 0056-0057; 0061. . Retrieved 2019/11/04.