S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[NH:11][C:10](=[O:20])[CH:9]=1.O>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:3][CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[NH:11][C:10](=[O:20])[CH:9]=13.4 ml (46.6 mmol) of thionyl chloride are added while stirring at room temperature to a suspension of 3.11 g (14.2 mmol) of 4-(2-hydroxyethyl)-6-methoxy-2(1H)-quinolone in 50 ml of chloroform and 3 drops of dimethylformamide. The suspension is heated to reflux for 14 hours (total solubilization). After cooling to room temperature, 50 ml of water are added dropwise to the reaction medium and the mixture is left stirring for 30 minutes. The organic phase is recovered, separated after settling has taken place, washed with water, dried over magnesium sulphate and filtered. The filtrate is concentrated under vacuum. 3.2 g of a pale yellow solid are obtained.
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