Ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• CAS No.: 127625-17-6
• Molecular Formula: C15H13ClN2O5
• Molecular Weight: 337
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID70363639
• Nikkaji Number: J665.074K
• Wikidata: Q82147370
• Mol file: 127625-17-6.mol

Synonyms:127625-17-6;ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate;ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydro-3-quinolinecarboxylate;ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxoquinoline-3-carboxylate;SCHEMBL10473197;DTXSID70363639;CFA62517;STK684301;AKOS005267246;AT35282;SB72398;CS-0321072;FT-0682978;1-Cyclopropyl-4-oxo-6-nitro-7-chloro-1,4-dihydroquinoline-3-carboxylic acid ethyl ester;ethyl7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

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

Chemical Property:

• Melting Point: >280 °C
• Boiling Point: 518.5±50.0 °C(Predicted)
• PKA: -8.35±0.40(Predicted)
• PSA: 94.12000
• Density: 1.531±0.06 g/cm3(Predicted)
• LogP: 3.59790
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 336.0512992
• Heavy Atom Count: 23
• Complexity: 569

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl7-Chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN(C2=CC(=C(C=C2C1=O)[N+](=O)[O-])Cl)C3CC3

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

There total 7 articles about Ethyl 7-chloro-1-cyclopropyl-6-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: 92.0%

ethyl ester of 3-cyclopropylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid (148926-95-8) → ethyl ester of 1-cyclopropyl-6-nitro-4-oxo-7-chloro-1,4-dihydroquinoline-3-carboxylic acid (127625-17-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 1h;

DOI:10.1021/jm00006a017

Reference yield:

2,4-dichloro-5-nitro benzoyl chloride (713-28-0) → ethyl ester of 1-cyclopropyl-6-nitro-4-oxo-7-chloro-1,4-dihydroquinoline-3-carboxylic acid (127625-17-6)

Guidance literature:

Multi-step reaction with 4 steps

2: 90 percent / 5 h / 20 °C

3: ethanol / 2 h / 20 °C

4: triethylamine / dimethylformamide / 3 h / 105 - 110 °C

With triethylamine; In ethanol; N,N-dimethyl-formamide; 1: Acylation / 2: Substitution / 3: Substitution / 4: Cyclization;

DOI:10.1007/BF02464110

Reference yield:

ethyl ester of 3-dimethylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid (148926-94-7) → ethyl ester of 1-cyclopropyl-6-nitro-4-oxo-7-chloro-1,4-dihydroquinoline-3-carboxylic acid (127625-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 2 h / 20 °C

2: triethylamine / dimethylformamide / 3 h / 105 - 110 °C

With triethylamine; In ethanol; N,N-dimethyl-formamide; 1: Substitution / 2: Cyclization;

DOI:10.1007/BF02464110

upstream raw materials:

ethyl ester of 3-cyclopropylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid

2,4-dichloro-5-nitro benzoyl chloride

ethyl ester of (5-nitro-2,4-dichlorobenzoyl)acetic acid

ethyl ester of 3-dimethylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid

Downstream raw materials:

6-amino-1-cyclopropyl-4-oxo-7-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

6-amino-1-cyclopropyl-7-[4-(2-methoxy-phenyl)-piperazin-1-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

1-cyclopropyl-6-nitro-4-oxo-7-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

1-cyclopropyl-7-[4-(2-methoxy-phenyl)-piperazin-1-yl]-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester