6-Hydroxymethylindole → 1H-Indole, 6-methyl-

HRID 864482Notes

Reaction equation

HRID 864482 reaction equation
O[CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1>C(O)C.[Pd].C(O)(=O)C>[CH3:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 27734596-Hydroxymethylindole

Product 1

HCID 1379281H-Indole, 6-methyl-

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

6-hydroxymethyl indole (6.135 g, 41.69 mmol) was dissolved in ethanol (70 ml). 10% Palladium on charcoal (0.610 g) was suspended in acetic acid (70 ml) and added to the ethanol (70 ml) solution. The mixture was placed on the high pressure hydrogenator at 60 psi. After 20 hours, the mixture was filtered through Celite and the resulting solution concentrated in vacuo. The mixture was purified by flash chromatography using chloroform as solvent to yield a colourless oil.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationthe resulting solution concentrated in vacuo
  3. customThe mixture was purified by flash chromatography
  4. customto yield a colourless oil

Sources & evidence

ORD record
ord-66e1a0d8687749b5b55b66226e35e529
Source dataset
uspto-grants-1996_10
Patent number
US05563147

Reaction notes

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