C([O:3][C:4]([C:6]1[C:7]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=[O:5])C.[OH-].[Na+]>C(O)C.O>[Cl:22][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)[C:6]([C:4]([OH:5])=[O:3])=[C:15]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1To a stirred solution of 6-chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acid ethyl ester (100 mg, 0.25 mmol) in ethanol (10 ml) was added 1N NaOH (1.26 ml, 1.26 mmol) solution at RT. The reaction mixture was refluxed for 24 h. The volatiles were removed under vacuum to afford a crude residue which was diluted with water. The aqueous layer was washed with ethyl acetate to remove non-polar impurities and then the pH was adjusted to 4-3 with 10% citric acid under cooling. Then the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to give a crude residue which was purified via Prep-HPLC followed by Prep-TLC to obtain pure 6-chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acid as pale yellow solid (14 mg, 15%). LC-MS: 369 (M+H)+.
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