[CH3:1][C:2]([OH:26])([CH3:25])[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1.C(O[K])=O>O.C1COCC1.[Pd]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:9]2[C:8]3[C:13](=[CH:14][C:5]([O:4][CH2:3][C:2]([CH3:25])([OH:26])[CH3:1])=[CH:6][CH:7]=3)[N:12]=[CH:11][CH:10]=2)=[CH:17][CH:18]=1To a solution of 2-methyl-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol (2.8 g, 7.9 mmol) and HCOOK (4.6 g, 55.3 mmol) in water (4 mL) and THF (12 mL) was added 10% Pd/C (0.24 g). The reaction mixture was stirred at 45° C. for 21 hours and then cooled to room temperature. The mixture was filtered through a Celite pad. The organic phase was separated and washed with brine (20 mL). The aqueous phase was extracted with EtOAc (15 mL). The combined organic phases were concentrated in vacuo and the residue was dried in vacuo at 50° C. overnight to give the title compound as a yellow solid (2.5 g, 97.7%).
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