Ethanol → 3-Amino-2-(1,1'-biphenyl)-4-yl-6-fluoro-4-quinolinecarboxylic acid

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A 21.35 g portion of 5-fluoroisatin was suspended in 175 ml of water in a three-necked 2 liter flask equipped with a reflux condenser and addition funnel. To the suspension was added a solution of 28.5 g of sodium hydroxide in 100 ml of water, then the mixture was heated to 90° C. A solution of 44.08 g of 2-amino-4'-phenylacetophenone, hydrochloride in 550 ml of a 1:1 mixture of ethanol:water was warmed slightly, then 200 ml of tetrahydrofuran was added to effect dissolution. This solution was added dropwise to the hot solution of 5-fluoroisatin over 2.75 hours with vigorous stirring. When addition was complete the solution was stirred at 90° C. for 2 hours, then the organic solvents were removed by distillation at 85° C. The remaining solution was cooled, added to 1 liter of water and the red solids collected, washed with water and saved. The filtrate was acidified to pH 5 with glacial acetic acid and the resulting yellow solid collected, washed with water and saved. The red solids saved above were stirred in a mixture of 3 liters of water and 100 ml of ammoninum hydroxide for 1 hour, then filtered and the filtrate acidified to pH 5 with glacial acetic acid. The resulting yellow solid was collected, washed with water, combined with the yellow solid saved above and dried, giving 26.9 g of the desired product, mp 229°-232° C. (dec.).

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