Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• CAS No.: 103772-12-9
• Molecular Formula: C₁₅H₁₁F₃N₂O₅
• Molecular Weight: 356.258
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID70554166
• Wikidata: Q82435042
• Mol file: 103772-12-9.mol

Synonyms:103772-12-9;Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate;ethyl 1-cyclopropyl-6,7,8-trifluoro-5-nitro-4-oxoquinoline-3-carboxylate;1-Cyclopropyl-5-Nitro-6,7,8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinoline Carboxylic Acid Ethyl Ester;1-Cyclopropyl-5-Nitro-6,7,8-Trifluoro-1,4-Dihydro-4-Oxo-3- Quinolinecarboxylic acid ethyl ester;PRNXYRWUZSNSFK-UHFFFAOYSA-N;SCHEMBL9248857;DTXSID70554166;AKOS015963352;Ethyl 1-Cyclopropyl-5-nitro-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Chemical Property of Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Chemical Property:

• Boiling Point: 511.3±50.0 °C(Predicted)
• PKA: -6.72±0.40(Predicted)
• PSA: 94.12000
• Density: 1.615±0.06 g/cm3(Predicted)
• LogP: 3.36180
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 356.06200594
• Heavy Atom Count: 25
• Complexity: 633

Purity/Quality:

97% ^*data from raw suppliers

1-CYCLOPROPYL-5-NITRO-6,7,8-TRIFLUORO-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER 95.00% ^*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(C1=O)C(=C(C(=C2F)F)F)[N+](=O)[O-])C3CC3

Technology Process of Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

There total 7 articles about Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-nitro-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:

2-nitro-3,4,5,6-tetrafluoro-β-oxobenzenepropanoic acid,ethyl ester (103772-11-8) + orthoformic acid triethyl ester (122-51-0) + Cyclopropylamine (765-30-0) → ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate (103772-12-9)

Guidance literature:

With potassium tert-butylate; Yield given. Multistep reaction; 1.) Ac₂O, 3.) t-BuOH;

DOI:10.1021/jm00398a003

Reference yield:

(Z)-3-Cyclopropylamino-2-(2,3,4,5-tetrafluoro-6-nitro-benzoyl)-acrylic acid ethyl ester → ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate (103772-12-9)

Guidance literature:

With potassium tert-butylate; at 60 ℃; for 6h; Yield given;

DOI:10.1021/jm00107a039

Reference yield:

2,3,4,5-tetrafluorobenzoic acid (1201-31-6) → ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate (103772-12-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 35 percent / fuming HNO₃, H₂SO₄ / 5.5 h / 70 °C

2: oxalyl chloride, DMF / CH₂Cl₂ / 16 h

3: 1.) n-BuLi, dipyridyl / 1.) THF, -30 deg C, 2.) THF, from -78 deg C to -35 deg C, 1 h

4: 95 percent / Ac₂O / 3 h / Heating

5: 2-methyl-propan-2-ol / 3.5 h / 45 °C

6: t-BuOK / 6 h / 60 °C

With n-butyllithium; dipyridyl; oxalyl dichloride; sulfuric acid; potassium tert-butylate; nitric acid; acetic anhydride; N,N-dimethyl-formamide; In dichloromethane; tert-butyl alcohol;

DOI:10.1021/jm00107a039

upstream raw materials:

2-nitro-3,4,5,6-tetrafluoro-β-oxobenzenepropanoic acid,ethyl ester

orthoformic acid triethyl ester

Cyclopropylamine

2,3,4,5-tetrafluorobenzoic acid

Downstream raw materials:

5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

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

5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid

5-amino-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid