[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)=[O:6])=[N+]=[N-].[ClH:15]>[Pd].CO>[ClH:15].[NH2:1][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)=[O:6]Palladium on carbon (10 wt %, 10.41 g, 9.78 mmol) was added to a solution of 2-azido-1-[3-(methyloxy)phenyl]ethanone (1.87 g, 9.78 mmol) and hydrochloric acid (8.14 mL, 98 mmol) in CH3OH (50 mL) under nitrogen, and the reaction mixture was stirred under hydrogen overnight at 25° C. The mixture was filtered, washing with CH2Cl2 (50 mL) and CH3OH (100 mL), and then concentrated. Water (150 mL) was added, and the mixture was lyophilized to afford an HCl salt of the title compound (2.0 g) as a brown solid. LC-MS (ES) m/z=166 [M+H]+.
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