[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:23])[CH2:21]Cl)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(=O)=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]2[CH2:21][O:23]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1A solution of 20 g (61 mmol) 8-benzyloxy-5-(2-chloro-1-hydroxy-ethyl)-1H-quinolin-2-one in 160 mL DMF is added dropwise at 0° C. to 35 mL of a 4 molar sodium hydroxide solution and then stirred for 2 hours at this temperature. The reaction mixture is combined with 1.5 L ice water, buffered by the addition of dry ice and extracted with ethyl acetate. The organic phases are dried with sodium sulphate, the solvent is distilled off and the residue is chromatographed over aluminium oxide (dichloromethane/ethyl acetate gradient). The fractions containing the product are evaporated down to 60 mL and then combined with petroleum ether, during which time a solid is precipitated, which is suction filtered and dried.
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