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

HRID 1791807Notes

Reaction equation

HRID 1791807 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-8ab4d48fa8a74ecd8be1088086b8319b
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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