2-(4-Nitrophenyl)-1,3-dioxolane → 4-(1,3-Dioxolan-2-yl)aniline

Reaktionsgleichung

C(=O)(O)[O-].[Na+].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[CH:11][CH:10]=1)([O-])=O>CCO.[Pt](=O)=O>[O:16]1[CH2:17][CH2:18][O:19][CH:15]1[C:12]1[CH:13]=[CH:14][C:9]([NH2:6])=[CH:10][CH:11]=1

Komponenten

Versuchsvorschrift

To a mixture of platinum dioxide (227 mg, 1.00 mmol) and sodium bicarbonate (420 mg, 5.00 mmol) under dry nitrogen was added a solution of 2-(4-nitrophenyl)-1,3-dioxolane (976 mg, 5.00 mmol) in EtOH (30.0 mL). The reaction mixture was bubbled with hydrogen for 15 min and then stirred under a hydrogen atmosphere (balloon) for 2 h. The reaction mixture was then filtered through a pad of Celite washing with MeOH. The filtrate was concentrated under reduced pressure to give the title compound (0.80 g, 96% yield).