7-Benzyloxy-1-methylindole → 1-methyl-1H-indol-7-ol

HRID 2220327

Reaction equation

HRID 2220327 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[N:16]([CH3:18])[CH:15]=[CH:14]2)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH3:18][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[OH:8])[CH:14]=[CH:15]1

Participants

5

Reactant 2

HCID 221368137-Benzyloxy-1-methylindoleHCID 178418361HCID 178418361, compound

Product 1

HCID 221368021-methyl-1H-indol-7-olYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7-benzyloxy-1methyl-1H-indole in 20 mL of ethanol was added 10% palladium on charcoal (0.2 g). This solution was stirred under balloon pressure hydrogen atmosphere for 4 h, then filtered through celite and concentrated in vacuo. This material was purified by flash chromatography, eluting silica gel with hexane:ethyl acetate (100:0 to 50:50) to give the product (0.58 g, 87%); Mass spectrum (TOF): m/z=147.1 (M).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. customThis material was purified by flash chromatography
  4. washeluting silica gel with hexane:ethyl acetate (100:0 to 50:50)

Sources & evidence

ORD record
ord-9f3a6c4a78474b19bcce4612e59c317d
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Linked notes

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