Ethanol → 5,6-Dihydroxyindole

HRID 1901981Notes

Reaction equation

HRID 1901981 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[N:7](C(OCC1C=CC=CC=1)=O)[CH2:6][CH2:5]2.C(O)C.C1CCCCC=1>[Pd].O>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[NH:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 702EthanolHCID 8079CyclohexeneHCID 15342429Phenylmethyl 2,3-dihydro-5,6-dihydroxy-1H-indole-1-carboxylate

Product 1

HCID 1146835,6-Dihydroxyindole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

11.4 g of benzyl 5,6-dihydroxy-2,3-dihydroindole-1-carboxylate, 60 ml of ethanol, 5.7 g of 10% palladium-on-charcoal, 5.7 ml of water and 23 ml of cyclohexene were mixed together, and the mixture was maintained at reflux for one hour.

Workup

  1. temperaturethe mixture was maintained
  2. temperatureat reflux for one hour

Sources & evidence

ORD record
ord-283210b8cc304fc78c2228be23766001
Source dataset
uspto-grants-1996_11
Patent number
US05578735

Reaction notes

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