Dimethylformamide → 6-[[2-(Acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Beteiligte Stoffe

Reaktionsschritte

A mixture of 1.73 g (13.2 mmol) of N-acetyl-L-alanine, 0.97 ml (13.2 mmol) of thionyl chloride, 1.02 ml (13.02 mmol) dimethylformamide, and 50 ml of dichloromethane is stirred at -20° to -30° for 20 minutes. A mixture of 2.45 g (12 mmol) of 6-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 5.04 ml (36 mmol) triethylamine, 4.57 ml (36 mmol) chlorotrimethylsilane and 100 ml of dichloromethane is stirred at room temperature for 25 minutes and is cooled to -60°. The cold acid chloride solution is added to the cold silylated quinoline and is stirred for 2 hours while the temperature comes up to 10°. The reaction mixture is evaporated to dryness and the residue is treated with water to give 2.60 g of 6-[[2-(acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 196°-200° .

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