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

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

5synthesis methods

Product Name:7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
CAS Number:100361-18-0
Molecular formula:C12H8ClFN2O3
Molecular Weight:282.65

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.

96568-07-9
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$45.00/1g

100361-18-0
214 suppliers
$13.00/5g

Yield:100361-18-0 78%

Reaction Conditions:

with hydrogenchloride;water in tetrahydrofuran; for 2 h;Reflux;Inert atmosphere;

Steps:

Compound 2: 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphtyridine-3-carboxylic acid

To a solution of ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphtyridine-3-carboxylate (0.1g, 0.32 mmol) in THF (5 ml) was added conc.HCl (45 μL, 0.7 mmol). The reaction mixture was heated to reflux for 2 h. After completion of the reaction by TLC, reaction mixture was cooled to room temperature. The solid precipitated was filtered to give the title compound as a solid (70 mg, 78%).

References:

Karoli, Tomislav;Mamidyala, Sreeman K.;Zuegg, Johannes;Fry, Scott R.;Tee, Ernest H.L.;Bradford, Tanya A.;Madala, Praveen K.;Huang, Johnny X.;Ramu, Soumya;Butler, Mark S.;Cooper, Matthew A. [Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,# 7,p. 2428 - 2433] Location in patent:supporting information; experimental part