5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Base Information

• Chemical Name: 5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 103772-14-1
• Molecular Formula: C13H9 F3 N2 O3
• Molecular Weight: 298.221
• DSSTox Substance ID: DTXSID70552369
• Nikkaji Number: J323.321I
• Wikidata: Q82432568
• Mol file: 103772-14-1.mol

Synonyms:103772-14-1;5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;5-AMINO-1-CYCLOPROPYL-6,7,8-TRIFLUORO-4-OXOQUINOLINE-3-CARBOXYLIC ACID;3-Quinolinecarboxylicacid, 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-;CQPUZLMNORVQPG-UHFFFAOYSA-N;SCHEMBL1345769;DTXSID70552369;5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid;5-Amino-l-Cyclopropyl-6,7, 8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinearboxylic Acid;1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4- dihydro-4-oxoquinoline-3-carboxylic acid;1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid;1-cyclopropyl-5-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid;1-cyclopropyl-5-amino-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;5-amino -1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline -3-carboxylic acid;5-amino-1-cyclopropyl -6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid;5-amino-1-cyclopropyl 6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;5-amino-1-cyclopropyl-6, 7, 8-trifluoro -1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;5-amino-1-cyclopropyl-6, 7, 8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;5-amino-1-cyclopropyl-6, 7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;5-amino-1-cyclopropyl-6,7, 8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid;5-amino-1-cyclopropyl-6,7,8-trifluoro -1,4-dihydro-4-oxoquinoline-3-carboxylic acid;5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4 -dihydro-4-oxo-3-quinolinecarboxylic acid;5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4 -oxo-3-quinolinecarboxylic acid;5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3quinolinecarboxylic acid;5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid;5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3 -carboxylic acid;5-amino-1-cyclopropyl-6,7,8-trifluoro1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Chemical Property of 5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.68
• Boiling Point: 512.4°Cat760mmHg
• Flash Point: 263.7°C
• PSA: 85.32000
• Density: 1.762g/cm³
• LogP: 2.61530
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 298.05652664
• Heavy Atom Count: 21
• Complexity: 523

Purity/Quality:

98% ^*data from raw suppliers

5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1N2C=C(C(=O)C3=C(C(=C(C(=C32)F)F)F)N)C(=O)O
• Uses: 5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid is an impurity of?Sparfloxacin (S679250), a?fluorianted quinolone antibacterial.

Technology Process of 5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

There total 16 articles about 5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 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: 100.0%

ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (103772-13-0) → 5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (103772-14-1)

Guidance literature:

With hydrogenchloride; for 2h; Heating;

DOI:10.1021/jm00107a039

Reference yield: 96.0%

ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate (110872-04-3) → 5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (103772-14-1)

Guidance literature:

With sulfuric acid; acetic acid; at 100 ℃; for 0.166667h;

DOI:10.1021/jm00168a018

Reference yield:

1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester (107564-02-3) → 5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (103772-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / triethylamine / toluene / 1 h / Heating

2: 96 percent / acetic acid, aq. H₂SO₄ / 0.17 h / 100 °C

With sulfuric acid; acetic acid; triethylamine; In toluene;

DOI:10.1021/jm00168a018

upstream raw materials:

ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate

ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate

2,3,4,5-tetrafluorobenzoic acid

Downstream raw materials:

5-Amino-1-cyclopropyl-6,8-difluoro-7-((R)-3-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

5-Amino-1-cyclopropyl-6,8-difluoro-7-[3-(4-Phenyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Ethyl 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate

Refernces

• 1、 Cociorva, Oana M.,Li, Bei,Nomanbhoy, Tyzoon,Li, Qiang,Nakamura, Ayako,Nakamura, Kai,Nomura, Masahiro,Okada, Kyoko,Seto, Shigeki,Yumoto, Kazuhiro,Liyanage, Marek,Zhang, Melissa C.,Aban, Arwin,Leen, Brandon,Szardenings, Anna Katrin,Rosenblum, Jonathan S.,Kozarich, John W.,Kohno, Yasushi,Shreder, Kevin R.. "Synthesis and structure-activity relationship of 4-quinolone-3-carboxylic acid based inhibitors of glycogen synthase kinase-3β". scheme or table. p. 5948 - 5951. Retrieved 2011/10/18.
• 2、 Domagala,Bridges,Culbertson,Gambino,Hagen,Karrick,Porter,Sanchez,Sesnie,Spense,Szotek,Wemple. "Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship". . p. 1142 - 1154. Retrieved 2007/10/02.