Ethanol → 1-methyl-1H-indol-6-ol

HRID 1198090Notes

Reaction equation

HRID 1198090 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.C1CCCCC=1.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 8079CyclohexeneHCID 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 consisting of 0.24 mole (57 g) of 6-benzyloxy-1-methylindole, 5.7 g of 10% palladium-on-charcoal, 114 ml of cyclohexene and 170 ml of 96% ethanol is heated for 30 minutes under reflux. The mixture is filtered hot to remove the catalyst. After evaporation of the filtrate under vacuum, an oil is obtained which, dissolved in isopropyl ether, gives the desired product after evaporation to dryness. It melts at 74° C.

Workup

  1. temperatureis heated for 30 minutes
  2. temperatureunder reflux
  3. filtrationThe mixture is filtered hot
  4. customto remove the catalyst
  5. customAfter evaporation of the filtrate under vacuum
  6. customan oil is obtained which

Sources & evidence

ORD record
ord-c8d3e5c97ada4d048c5411a371550955
Source dataset
uspto-grants-1994_01
Patent number
US05279620

Reaction notes

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