Methanol → 6-Methoxy-1H-indol-5-ol

HRID 1043113Notes

Reaction equation

HRID 1043113 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-1f7e9b5ee4ee4f0c990cb6f98d809ff5
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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