HCID 19890450, compound → HCID 18699345, compound

HRID 893550Notes

Reaction equation

HRID 893550 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[O:18][CH2:19][CH2:20][CH2:21][CH3:22])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH2:19]([O:18][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:9]=1[OH:8])[NH:15][CH:14]=[CH:13]2)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 19890450HCID 19890450, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18699345HCID 18699345, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Benzyloxy 5-butoxy indole (4 g, 0.0135 mole) is hydrogenated under 50 atmospheres of hydrogen in a reactor with 40 ml of ethanol and 0.6 g 10% palladium on carbon for 3 hours. After filtration and evaporation of the solvent, the residue is recrystallized in a mixture of benzene-hexane to produce 5-butoxy 6-hydroxy indole (2.5 g, yield 90%).

Workup

  1. filtrationAfter filtration and evaporation of the solvent
  2. customthe residue is recrystallized in a mixture of benzene-hexane

Sources & evidence

ORD record
ord-886432aa26414a84956e5430304dbab0
Source dataset
uspto-grants-1992_06
Patent number
US05126125

Reaction notes

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