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100361-18-0

100361-18-0 Structure

100361-18-0 Structure
IdentificationBack Directory
[Name]

7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
[CAS]

100361-18-0
[Synonyms]

7-Chloro-1-cycloprop
Nalidixic acid cyclopropyl
7-Chloro-1-cyclopropyl-6-fluor
Gemifloxacin 7-Chloro Impurity
8-naphthyridine-3-carboxylic acid
7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1
1-Cyclopropyl-6-fluoro-7-chloride-4-oxo-1
(S)-2-aMino-3-(2,4-diMethylphenyl)propanoic acid
7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-Ox
1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyl ridine carbox.acid
7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
7-Chloro-1-cyclopropyl-1,4-dihydro-3-oxo-1,8-naphthyridine-3-carboxylic aci
1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYLPYRIDINECARBOXYLIC ACID
3-Carboxy-7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine
7-Chloro-1-Cyclopropyl-6-Fluoro-1,4-Dihydro-4-Qxoquinoline-3-CarboxylicAcid98%
1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYLRIDINE CARBOXYLIC ACID 99%
7-Chloro-1-Cyclopropyl-6-Fluoro-4-Oxo-1,4-Dihydro-1,8-Naphthyridine-3-Carboxylic
7-Chloro-1-Cyclopropyl-6-Fluoro-4-Oxo-1,4-Dihydro-1,8-Naphthyridine-3-CarboxylicAci
7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylicacid
1-Cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-1,8-napthyridine-3-carboxylic acid
7-Chloro-1-Cyclopropyl-6-Fluoro-4-Oxo-1,4-Dihydro-1,8-Naphthyridin-3-Carboxylic Acid
7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
1-Cyclopropyl-6-Fluoro-7-Chloro-4-Oxo-1,4-Dihydro-1,8-Naphthyridine-3-Carboxylie acid
1-Cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
1-CYCLOPROPYL-6-FLUORO-7-CHLORIDE-4-OXO-1,4-DIHYDRO-1,8-NAPTHYRIDINE-3-CARBOXYLIE ACID
1-CYCLOPROPYL-6-FLUORO-7-CHLORIDE-4-OXO-1,4-DIHYDRO-1,8-NAPTHYRIDINE-3-CARBOXYLIC ACID
1,8-Naphthyridine-3-carboxylicacid, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-
1-Cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid, 95+%
[EINECS(EC#)]

600-082-3
[Molecular Formula]

C12H8ClFN2O3
[MDL Number]

MFCD08458865
[MOL File]

100361-18-0.mol
[Molecular Weight]

282.65
Chemical PropertiesBack Directory
[Melting point ]

209-212 °C
[Boiling point ]

485.9±45.0 °C(Predicted)
[density ]

1.727±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Room Temperature
[form ]

powder to crystal
[pka]

5.96±0.70(Predicted)
[color ]

White to Almost white
[CAS DataBase Reference]

100361-18-0
Safety DataBack Directory
[HS Code ]

2933998090
Hazard InformationBack Directory
[Chemical Properties]

Off-white or light yellow powder
[Uses]

Gemifloxacin intermediate as antibacterial agent
[Synthesis]

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid Ethyl Ester

96568-07-9

7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

100361-18-0

Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (0.1 g, 0.32 mmol) was used as a raw material and dissolved in THF (5 ml). Concentrated HCl (45 μL, 0.7 mmol) was added to this solution. The reaction mixture was heated to reflux and the reaction was continued for 2 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the reaction mixture was cooled to room temperature. The precipitated solid was collected by filtration to afford the target product 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid in a yield of 70 mg with 78% yield.

[References]

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 7, p. 2428 - 2433
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 25, p. 5564 - 5575
[3] Patent: WO2005/40164, 2005, A1. Location in patent: Page/Page column 10-12
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