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

Base Information

• Chemical Name: 5-Amino-1-cyclopropyl-6,7-difluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 167888-38-2
• Molecular Formula: C₁₄H₁₂F₂N₂O₃
• Molecular Weight: 294.258
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID60445852
• Nikkaji Number: J747.755D
• Wikidata: Q82264387
• Mol file: 167888-38-2.mol

Synonyms:167888-38-2;5-AMINO-1-CYCLOPROPYL-6,7-DIFLUORO-8-METHYL-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID;5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxo-3-quinolinecarbocylic acid;5-amino-1-cyclopropyl-6,7-difluoro-8-methyl-4-oxoquinoline-3-carboxylic acid;5-AMINO-1-CYCLOPROPYL-6,7-DIFLUORO-1,4-DIHYDRO-8-METHYL-4-OXO-3-QUINOLINECARBOXYLIC ACID;SCHEMBL500723;DTXSID60445852;C14H12F2N2O3;MFCD04972495;AKOS015961263;AB21133;3-Quinolinecarboxylic acid, 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxo-;5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid;AC-13103;WS-01998;CS-0360677;W14698;J-010405;1-Cyclopropyl-4-oxo-5-amino-6,7-difluoro-8-methyl-1,4-dihydroquinoline-3-carboxylic acid;5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxlic acid;5-AMINO-1-CYCLOPROPYL-6,7-DIFLUORO-8-METHYL-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLICACID

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.683
• Boiling Point: 523.1°Cat760mmHg
• PKA: 6.38±0.50(Predicted)
• Flash Point: 270.2°C
• PSA: 85.32000
• Density: 1.623g/cm³
• LogP: 2.78460
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 294.08159857
• Heavy Atom Count: 21
• Complexity: 520

Purity/Quality:

98%min ^*data from raw suppliers

5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxo-3-quinolinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(=C(C(=C1F)F)N)C(=O)C(=CN2C3CC3)C(=O)O
• Uses: 5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxo-3-quinolinecarboxylic Acid is an antibacterial agent.

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

There total 10 articles about 5-Amino-1-cyclopropyl-6,7-difluoro-8-methyl-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: 87.0%

ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate (167888-37-1) → 5-amino-1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (167888-38-2)

Guidance literature:

With hydrogenchloride; acetic acid; for 2h; Heating;

DOI:10.1248/cpb.44.1074

Reference yield:

3-methyl-2,4,5-trifluorobenzoic acid (112822-85-2) → 5-amino-1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (167888-38-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 41 percent / 70percent aq.HNO₃, conc.H₂SO₄ / 2 h / Ambient temperature

2: (COCl)2 / CH₂Cl₂; dimethylformamide / 2 h / Ambient temperature

3: 1.) EtOH, Mg / 1.) toluene, 2.) toluene, RT, 2 h

4: p-TsOH / H₂O / 0.83 h / Heating

5: 34 percent / Ac₂O / 1 h / Heating

6: 23.3 g / ethanol / 0.5 h / Ambient temperature

7: 85 percent / K₂CO₃, 18-crown-6-ether / tetrahydrofuran / 8 h / 70 °C

8: 90 percent / Fe, AcOH / 4.5 h / 90 °C

9: 87 percent / conc.HCl, AcOH / 2 h / Heating

With hydrogenchloride; oxalyl dichloride; 18-crown-6 ether; ethanol; sulfuric acid; nitric acid; acetic anhydride; iron; potassium carbonate; toluene-4-sulfonic acid; magnesium; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.44.1074

Reference yield:

2,4,5-Trifluoro-3-methyl-6-nitrobenzoic acid (167887-95-8) → 5-amino-1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (167888-38-2)

Guidance literature:

Multi-step reaction with 8 steps

1: (COCl)2 / CH₂Cl₂; dimethylformamide / 2 h / Ambient temperature

2: 1.) EtOH, Mg / 1.) toluene, 2.) toluene, RT, 2 h

3: p-TsOH / H₂O / 0.83 h / Heating

4: 34 percent / Ac₂O / 1 h / Heating

5: 23.3 g / ethanol / 0.5 h / Ambient temperature

6: 85 percent / K₂CO₃, 18-crown-6-ether / tetrahydrofuran / 8 h / 70 °C

7: 90 percent / Fe, AcOH / 4.5 h / 90 °C

8: 87 percent / conc.HCl, AcOH / 2 h / Heating

With hydrogenchloride; oxalyl dichloride; 18-crown-6 ether; ethanol; acetic anhydride; iron; potassium carbonate; toluene-4-sulfonic acid; magnesium; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.44.1074

upstream raw materials:

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

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

2,4,5-Trifluoro-3-methyl-6-nitrobenzoic acid

2,4,5-trifluoro-3-methyl-6-nitrobenzoyl chloride

Downstream raw materials:

HSR-903