Hydrochloric Acid → HCID 58841411, compound

Reaction equation

[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[N:16]O)[CH2:11][CH2:10][CH2:9]2.Cl>[Pd].CCO>[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]([NH2:16])[CH2:11][CH2:10][CH2:9]2

Participants

Procedure

A mixture of 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one oxime (0.3 g, 1.2 mmol), EtOH (12 mL), Pd/C (Aldrich, 0.13g, 0.12 mmol), and concentrated HCl (0.24 mL) was purged with H2 and connected to a H2 balloon overnight at RT. The catalyst was filtered through Celite® and washed with MeOH. The filtrate was concentrated in vacuo. The residue was added saturated NaHCO3 and extracted with CH2Cl2. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (5%-10% MeOH—CH2Cl2) to afford the compound as a colorless oil. MS (ESI): 235 (M+H)+.