Sodium Hydroxide → 2,3-dihydro-1H-indol-5-ol

HRID 1640256Notes

Reaction equation

HRID 1640256 reaction equation
C([BH3-])#N.[Na+].[OH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.[OH-].[Na+]>C(O)(=O)C>[NH:11]1[C:12]2[C:8](=[CH:7][C:6]([OH:5])=[CH:14][CH:13]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 160545-HydroxyindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 100346842,3-dihydro-1H-indol-5-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under a nitrogen atmosphere 0.34 g sodium cyanoborohydride were added batchwise to 0.60 g (4.5 mmol) 5-hydroxyindole in 5.0 mL glacial acetic acid and the mixture was stirred for 60 min at RT. Then the reaction mixture was poured onto a 4N aqueous sodium hydroxide solution and extracted with EtOAc. The combined organic phases were washed several times with saturated sodium hydrogen carbonate solution, dried on sodium sulphate and evaporated down.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phases were washed several times with saturated sodium hydrogen carbonate solution
  3. customdried on sodium sulphate
  4. customevaporated down

Sources & evidence

ORD record
ord-7fb701233e8b4271a07233300e72cd16
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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