[CH:1]1([O:6][C:7]2[C:8]([N+:20]([O-])=O)=[N:9][CH:10]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=2)[CH2:5]CCC1.O.[C:24](O)(=[O:26])C>[Zn]>[CH3:24][O:26][CH2:5][CH2:1][O:6][C:7]1[C:8]([NH2:20])=[N:9][CH:10]=[C:11]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=13-Cyclopentyloxy-2-nitro-5-phenoxy-pyridine (0.46 mmol) is dissolved in acetic acid (1.5 ml). After addition of water (1.5 ml), zinc powder (6.2 eq.) is added and the reaction suspension is heated to 100° C. for 3 h. The reaction suspension is cooled to room temperature and filtrated. The filtrate is pored into 3.5% NaOH (30 ml) and extracted with dichloromethane. The combined organic layers are washed with brine, dried over MgSO4 and the solvent is removed in vacuo. 3-(2-Methoxyethoxy)-5-phenoxy-pyridine-2-ylamine is obtained as brown oil in a yield of 72%; HPLC (method C): 1.43 min; LC-MS (method A): 1.231 min, 271.15 (M+H+).
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