6-Tert-butoxy-2-tert-butyl-5-nitro-1H-indole → 6-tert-butoxy-2-tert-butyl-1H-indol-5-amine

HRID 503313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503313
[C:1]([O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[NH:12]2)=[CH:8][C:7]=1[N+:19]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[NH:12]2)=[CH:8][C:7]=1[NH2:19])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 534216126-Tert-butoxy-2-tert-butyl-5-nitro-1H-indole

Produkt 1

HCID 591291526-tert-butoxy-2-tert-butyl-1H-indol-5-amineAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of 6-tert-butoxy-2-tert-butyl-5-nitro-1H-indole (100 mg, 0.36 mmol) and Raney Ni (0.5 g) in MeOH (15 mL) was stirred under H2 atmosphere (1 atm) at the room temperature for 2.5 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to dryness. The residue was recrystallized in ether to give 6-tert-butoxy-2-tert-butyl-1H-indol-5-amine (30 mg, 32%). 1H-NMR (300 MHz, MeOD) 6.98 (s, 1H), 6.90 (s, 1H), 5.94 (d, J=0.6 Hz, 1H), 1.42 (s, 9H), 1.36 (s, 9H); MS (ESI) m/e 205.0.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure to dryness
  3. customThe residue was recrystallized in ether

Quellen und Nachweise

ORD-Eintrag
ord-65dba9012157466b82afae136ba95f9f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776905B2

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