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
105 suppliers
$45.00/1g

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

100361-18-0
215 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