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

HRID 654394Notes

Reaction equation

HRID 654394 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.C(O)C>[Pd].C1CCCCC1>[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 702EthanolHCID 189625274-Benzyloxy-2,3-dimethyl-7-methoxyindole

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8078CyclohexaneSolvent

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 have been added 80 ml of cyclohexane 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-2e711e5a1e3e4744a6a090b4600470fa
Source dataset
uspto-grants-1992_07
Patent number
US05131911

Reaction notes

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