Cyclohexene → 2,3-Dimethyl-4-hydroxy-7-methoxyindole

HRID 1707755Notes

Reaction equation

HRID 1707755 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]2[C:10]=1[C:11]([CH3:21])=[C:12]([CH3:20])[NH:13]2)C1C=CC=CC=1.C1CCCCC=1>[Pd].C(O)C>[CH3:20][C:12]1[NH:13][C:14]2[C:10]([C:11]=1[CH3:21])=[C:9]([OH:8])[CH:17]=[CH:16][C:15]=2[O:18][CH3:19]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 189625274-Benzyloxy-2,3-dimethyl-7-methoxyindole

Product 1

HCID 184594912,3-Dimethyl-4-hydroxy-7-methoxyindole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.14 mole (39.5 g) of 4-benzyloxy-2,3-dimethyl-7-methoxyindole and 4 g of 10% palladium-on-charcoal in 120 ml of 96° ethanol to which has been added 80 ml of cyclohexene is heated under reflux. After 1 hour 30 minutes the catalyst is removed by hot filtration. The desired product is obtained by concentrating the filtrate to dryness. It is purified by dissolving it hot in isopropyl ether, filtering in the presence of charcoal and evaporating the filtrate to dryness. It melts at 164° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. customAfter 1 hour 30 minutes the catalyst is removed by hot filtration

Sources & evidence

ORD record
ord-0301f58703a7447a941cc2925012897b
Source dataset
uspto-grants-1994_10
Patent number
US05354870

Reaction notes

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