N-Methyl-5-benzyloxyindole → 1-Methyl-1H-indol-5-ol

HRID 454288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454288
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[CH:12]2)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[CH:12]2

Komponenten

5

Edukt 2

HCID 259196N-Methyl-5-benzyloxyindoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 108445251-Methyl-1H-indol-5-olAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 5-benzyloxy-1-methylindole (3.5 g, 15.7 mmol), in ethanol (100 ml) was hydrogenated at ambient temperature and 1 atmosphere pressure hydrogen for 4 hours using 10% palladium on carbon (0.5 g) as catalyst. The catalyst was filtered off and the filtrate evaporated in vacuo. The residue was purified by silica column chromatography eluting with ethyl acetate/dichloromethane (10/90) to give 5-hydroxy-1-methylindole (2.1 g, 97%).

Aufarbeitung

  1. customwas hydrogenated at ambient temperature
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was purified by silica column chromatography
  5. washeluting with ethyl acetate/dichloromethane (10/90)

Quellen und Nachweise

ORD-Eintrag
ord-84a72863aaa846bda8f2d1f2f22ab9f7
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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