1-Benzyl-5-nitro-1H-indole → 1-Benzyl-1H-indol-5-ylamine

HRID 1936746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1936746
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]=[CH:10]2

Komponenten

6

Edukt 2

HCID 98563511-Benzyl-5-nitro-1H-indoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 27946241-Benzyl-1H-indol-5-ylamineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1-benzyl-5-nitroindole (0.51 g, 0.02 mol) in a mixture of ethyl acetate (25 ml) and methanol (25 ml) was carefully added to 10% palladium on charcoal (45 mg). The resulting suspension was stirred at room temperature under an atmosphere of hydrogen. When the reaction was complete (indicated by tlc or calculated uptake of hydrogen) the suspension was filtered through a pad of Harbolite™, and the filtrate evaporated to dryness to give 5-amino-1-benzylindole (0.40 g, 91%) as an off-white solid; m.p. 66-68° C.; δH [2H6]-DMSO 7.30-7.12 (6H, m, 2-H, 2″-H, 3″-H, 4″-H, 5″-H, 6″-H), 7.08 (1H, d, J 8, 7-H), 6.70 (1H, s, 4-H), 6.49 (1H, d, J 8, 6-H), 6.18 (1H, s, 3-H), 5.28 (2H, s, CH2), 4.38 (2H, br s, NH2).

Aufarbeitung

  1. filtrationwas filtered through a pad of Harbolite™
  2. customthe filtrate evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4714864a6f8647a699ca64072ce9367c
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06391874B1

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