Dimethylformamide → 1,4-Dihydro-4-oxo-6-[[(5-oxo-2-pyrrolidinyl)carbonyl]-amino]-3-quinolinecarboxylic acid

Beteiligte Stoffe

Reaktionsschritte

A mixture of 1.94 g (15 mmol) of 5-oxo-L-proline, 1.1 ml (15 mol) dimethylformamide, and 30 ml of dichloromethane is stirred 0°-5° for 1 hour. A mixture of 2.04 g (10 mmol) of 6-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, [J. Pharm. Sci., 11, 1051 (1963)] 4.2 ml (30 mmol) of triethylamine, 3.8 ml (30 mmol) of chlorotrimethylsilane, and 75 ml of dichloromethane is stirred at room temperature for 40 minutes and then is cooled at 0°. The cold acid chloride solution is added to the cold silylated quinoline and is stirred at 5° for 4 hours and overnight at room temperature. The reaction mixture is evaporated and the residue is treated with water to give 1.81 g of 1,4-dihydro-4-oxo-6-[[(5-oxo-2-pyrrolidinyl)carbonyl]-amino]-3-quinolinecarboxylic acid.

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