Uses
7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid is a 1-arylated derivative of 1,4-dihydro-4-oxoquinoline-3-carboxylic acid with antibacterial activity.
Synthesis
1-(p-Fluoro-phenyl)-6-fluoro-7-chloro-4-oxo-3-quinolinecarboxylic acid was synthesised by a three-step procedure. Step 1: Preparation of 2,4-dichloro-5-fluoroacetophenone. 2,4-Dichlorofluorobenzene undergoes a Friedel-Crafts reaction with AcCl catalyzed by anhydrous AlCl3. Step 2: Preparation of methyl -(2,4-dichloro-5-fluorobenzoyl)--(4-fluoroanilino)acrylate. The ketone from step 1 reacts with (MeO)2CO and NaH, then with a dimethyl sulfate/DMF complex. Water is added, followed by p-fluoroaniline to give the product. Step 3: Preparation of 7-chloro-6-fluoro-1-p-fluorophenyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. The product from step 2 reacts with NaH in chlorobenzene. NaOH solution is then added for hydrolysis. Acidification precipitates the product.
