3-Quinolinecarboxylic acid,1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-

Base Information

• Chemical Name: 3-Quinolinecarboxylic acid,1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-
• CAS No.: 130579-27-0
• Molecular Formula: C13H10FNO4
• Molecular Weight: 263.225
• European Community (EC) Number: 847-486-8
• Nikkaji Number: J2.015.013K
• Mol file: 130579-27-0.mol

Synonyms:3-quinolinecarboxylic acid,1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-;130579-27-0;SCHEMBL4299077;GLPHFHRWJZECNZ-UHFFFAOYSA-N;1-cyclopropyl-1,4-dihydro-6-fluoro-7-hydroxy-4-oxo-quinoline-3-carboxylic acid;1-cyclopropyl-6-fluoro-7-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property of 3-Quinolinecarboxylic acid,1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 263.05938596
• Heavy Atom Count: 19
• Complexity: 460

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC1N2C=C(C(=O)C3=CC(=C(C=C32)O)F)C(=O)O

Technology Process of 3-Quinolinecarboxylic acid,1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-

There total 1 articles about 3-Quinolinecarboxylic acid,1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo- 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:

piperazine (110-85-0) + 1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2,83329-50-4) + 3-Cyclopropylamino-2-(2,4,5-trifluorbenzoyl)acrylsaeure-ethylester (101799-76-2) → ciprofloxacin (85721-33-1,178489-05-9,189257-90-7) + C22H26FN3O4 + 1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-3-quinoline-carboxylic acid (130579-27-0)

Guidance literature:

piperazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-Cyclopropylamino-2-(2,4,5-trifluorbenzoyl)acrylsaeure-ethylester; at 180 ℃; for 0.116667h; Flow reactor;

With tetra(n-butyl)ammonium hydroxide; In water; at 150 ℃; under 9050.33 Torr; Temperature; Flow reactor;

DOI:10.1021/acs.oprd.1c00118

Reference yield:

1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-3-quinoline-carboxylic acid (130579-27-0) → 7-{4-[(S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 0 - 20 °C

2: 20 °C

3: Pd(PPh₃)2Cl₂; aq. K₂HPO₄ / 1,2-dimethoxy-ethane / 90 °C

4: TFA / CH₂Cl₂

5: pyridine

6: H₂ / Pd/C / ethanol

With pyridine; bis-triphenylphosphine-palladium(II) chloride; dipotassium hydrogenphosphate; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In 1,2-dimethoxyethane; ethanol; dichloromethane;

DOI:10.1016/j.bmcl.2003.07.021

Reference yield:

1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-3-quinoline-carboxylic acid (130579-27-0) → 7-[4-((S)-5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid benzyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 0 - 20 °C

2: 20 °C

3: Pd(PPh₃)2Cl₂; aq. K₂HPO₄ / 1,2-dimethoxy-ethane / 90 °C

4: TFA / CH₂Cl₂

With pyridine; bis-triphenylphosphine-palladium(II) chloride; dipotassium hydrogenphosphate; trifluoroacetic acid; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1016/j.bmcl.2003.07.021

upstream raw materials:

piperazine

1,8-diazabicyclo[5.4.0]undec-7-ene

3-Cyclopropylamino-2-(2,4,5-trifluorbenzoyl)acrylsaeure-ethylester

Downstream raw materials:

Benzyl-1-cyclopropyl-6-fluoro-4-oxo-7-{[(trifluoromethyl)sulfonyl]oxy}-1,4-dihydro-3-quinolinecarboxylate

Benzyl-7-(4-{(5S)-5-{(acetylamino)methyl}-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate

7-{4-[5-(tert-butoxycarbonylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid benzyl ester