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

HRID 844528Notes

Reaction equation

HRID 844528 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][C:9](O)=[C:10]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][C:12]=3[OH:21])[C:4]2=[CH:3][CH:2]=1.[NH3:23]>>[NH2:23][C:9]1[CH:8]=[CH:7][C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:10]=1[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[OH:21]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 11762Binol

Product 1

HCID 36177972'-Amino-1,1'-binaphthalen-2-olYield 91%

Conditions

Temperature
200 °C

Procedure

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).

Workup

  1. temperaturecooled down to ambient temperature
  2. filtrationfiltered
  3. washThe resulting solid was washed with water
  4. customfollowed by recrystallization from benzene

Sources & evidence

ORD record
ord-df66876587ff498492fcbd00dd740111
Source dataset
uspto-grants-2002_04
Patent number
US06380392B1

Reaction notes

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