2-Aminofluorenone → 2-amino-9H-fluoren-9-ol
Reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:15])[C:4]=2[CH:3]=1.[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([OH:15])[C:4]=2[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Commercially available 2-amino-9-fluorenone 1 (10 mmol) was dissolved in 100 mL of methanol and 0.38 g (10 mmol) of sodium borohydride was added. The mixture was stirred at 25° C. for 1 h and concentrated to dryness under vacuum. The residue was suspended in 100 mL of saturated aqueous NaHCO3− and extracted with ethylacetate (100 mL). The ethylacetate layer was concentrated under vacuum and the residue was crystallized from ethylacetate/hexane (2:1) to afford 1.4 g of pure 2-amino-9-hydroxyfluorene 2.
Workup
- concentrationconcentrated to dryness under vacuum
- extractionextracted with ethylacetate (100 mL)
- concentrationThe ethylacetate layer was concentrated under vacuum
- customthe residue was crystallized from ethylacetate/hexane (2:1)
Sources & evidence
- ORD record
- ord-848fbf565390494d987dedbc835b2070
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706753B2
Reaction notes
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