Methanol → 6-Methoxy-1H-indol-5-ol

HRID 624380Notes

Reaction equation

HRID 624380 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][CH:13]=[CH:12]2)C1C=CC=CC=1.CO.[H][H]>[OH-].[OH-].[Pd+2].C(OCC)(=O)C>[CH3:19][O:18][C:17]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][NH:14]2)=[CH:10][C:9]=1[OH:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 2608005-Benzyloxy-6-methoxyindoleHCID 178418361HCID 178418361, compound

Product 1

HCID 1649576-Methoxy-1H-indol-5-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(benzyloxy)-6-methoxy-1H-indole (3.00 g) was added to methanol (100 mL) and ethyl acetate (100 mL) in a pressure bottle. Palladium hydroxide on carbon (0.832 g) was added and the solution was shaken under 30 psi of hydrogen at room temperature for 40 minutes. The mixture was filtered through a nylon membrane, the solvent removed under vacuum, the residue taken up in ethyl acetate, the solution was filtered over a pad of silica gel, and the solvent was removed from the filtrate under vacuum.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. customthe solvent removed under vacuum
  3. filtrationthe solution was filtered over a pad of silica gel
  4. customthe solvent was removed from the filtrate under vacuum

Sources & evidence

ORD record
ord-bf64eb067f644eb1ac2abfe43f46c627
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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