N-Methyl-5-benzyloxyindole → 1-Methyl-1H-indol-5-ol

HRID 454288Notes

Reaction equation

HRID 454288 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[CH:12]2)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[CH:12]2

Participants

5

Reactant 2

HCID 259196N-Methyl-5-benzyloxyindoleHCID 178418361HCID 178418361, compound

Product 1

HCID 108445251-Methyl-1H-indol-5-olYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-benzyloxy-1-methylindole (3.5 g, 15.7 mmol), in ethanol (100 ml) was hydrogenated at ambient temperature and 1 atmosphere pressure hydrogen for 4 hours using 10% palladium on carbon (0.5 g) as catalyst. The catalyst was filtered off and the filtrate evaporated in vacuo. The residue was purified by silica column chromatography eluting with ethyl acetate/dichloromethane (10/90) to give 5-hydroxy-1-methylindole (2.1 g, 97%).

Workup

  1. customwas hydrogenated at ambient temperature
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was purified by silica column chromatography
  5. washeluting with ethyl acetate/dichloromethane (10/90)

Sources & evidence

ORD record
ord-84a72863aaa846bda8f2d1f2f22ab9f7
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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