Nitrogen → 6-Hydroxyindole

HRID 1769880Notes

Reaction equation

HRID 1769880 reaction equation
C1(C[O:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[CH:14][NH:15]3)=[CH:11][CH:10]=2)C=CC=CC=1.N#N>CC(C)=O.[Pd]>[OH:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 2608046-(benzyloxy)-1H-indole

Product 1

HCID 5245086-HydroxyindoleYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

6-Phenylmethoxyindole (3.93 g, 17.6 mmol), was suspended in acetone (350 mL), under N2 and cooled in an ice bath. 10% Palladium on carbon (0.80 g) was added, and the N2 atmosphere was replaced with H2 by alternately placing the reaction flask under vacuum and introducing H2 from a balloon. The cold bath was then removed and the reaction mixture stirred under positive H2 pressure for 16 hours. The reaction mixture was cooled in an ice bath, and N2 reintroduced. The reaction mixture was filtered through a pad of celite and concentrated in vacuo. The crude product was purified by chromatography on silica gel to give 6-hydroxyindole (1.70 g, 73%).

Workup

  1. temperaturecooled in an ice bath
  2. additionintroducing H2 from a balloon
  3. customThe cold bath was then removed
  4. temperatureThe reaction mixture was cooled in an ice bath
  5. additionN2 reintroduced
  6. filtrationThe reaction mixture was filtered through a pad of celite
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a403db07c6d64cefab50998b86dd5c3c
Source dataset
uspto-grants-1995_01
Patent number
US05382670

Reaction notes

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