Ammonia → 2'-Amino-1,1'-binaphthalen-2-ol

Participants

Reaction Conditions

Reaction Steps

To a 125 mL Teflon lined autoclave was added 5 g (17.5 mmol) of 1,1′-bi-2-naphthol, 23.47 g (175 mmol) of (NH4)2SO3H2O and 65 mL of concentrated aqueous ammonia. The mixture was heated in an oil-bath to 200° C. for 5 days, then cooled down to ambient temperature and filtered. The resulting solid was washed with water followed by recrystallization from benzene to afford 4.52 g (15.8 mmol, 91%) of pure 2-amino-2′-hydroxy-1,1′-binaphthyl. Enantiomerically pure NOBIN can be obtained by the resolution methods reported in the literature (Ding, K.; Wang, Y.; Yun, H.; Lin, J.; Wu, Y.; Terada, M.; Okubs, Y.; Mikami, K.; Chem. Eur. J. 1999, 5, 1734-1737).

Provenance & Evidence