Ethanol → 1-methyl-1H-indol-6-ol

HRID 1086953Notes

Reaction equation

HRID 1086953 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH3:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.C1CCCCC1.C(O)C>C(OC(C)C)(C)C.[Pd]>[OH:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH3:18])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8078CyclohexaneHCID 123483846-(Benzyloxy)-1-methyl-1H-indole

Product 1

HCID 122034961-methyl-1H-indol-6-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7914Diisopropyl EtherSolvent

Procedure

The mixture constituted by 0.24 mole (57 g) 6-benzyloxy-1-methylindole, 5.7 g 10% palladium-on-charcoal, 114 ml cyclohexane and 170 ml 96° ethanol is heated for 30 minutes under reflux. It is filtered hot in order to remove the catalyst. After evaporation of the filtrate under vacuum, an oil is obtained which, when dissolved in isopropyl ether, leads after evaporation to dryness to the desired product. It melts at 74° C.

Workup

  1. temperatureis heated for 30 minutes
  2. temperatureunder reflux
  3. filtrationIt is filtered hot in order
  4. customto remove the catalyst
  5. customAfter evaporation of the filtrate under vacuum
  6. customan oil is obtained which, when
  7. customafter evaporation to dryness to the desired product

Sources & evidence

ORD record
ord-84f3212edfae4471b1c61c4278551ffb
Source dataset
uspto-grants-1991_07
Patent number
US05034015

Reaction notes

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