N,N,N',N',N'',N''-Hexamethylmethanetriamine → 5-phenoxy-1H-indole

HRID 1371890

Reaktionsgleichung

Reaktionsgleichung von HRID 1371890
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH3:17])([O-])=O.[CH3:18]N(C(N(C)C)N(C)C)C.[H][H]>C1(C)C=CC=CC=1.CCOC(C)=O.[Pd]>[O:10]([C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[NH:1][CH:18]=[CH:17]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 3

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 27284182-Nitro-5-phenoxytolueneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 112412535-phenoxy-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Combine 2-nitro-5-phenoxytoluene (1.15 g, 5.0 mmol) and tris(dimethylamino)methane (0.87 g, 6.0 mmol) in 10 mL dry toluene and heat to reflux under nitrogen. After 2 hours, cool the reaction mixture to room temperature and evaporate the toluene under reduced pressure to form a residue. Dissolve the residue in 15 mL EtOAc, mix with Pd/C (10%, 100 mg), stir at room temperature under 1 atmosphere of hydrogen for 1.5 days. Filter off catalyst and concentrate the filtrate. Chromatograph on silica gel eluting with hexanes/EtOAc give the title compound as a solid: 1H NMR (300 MHz, CDCl3) 6.49–6.50 (m, 1H), 6.93–7.03 (m, 4H), 7.22–7.27 (m, 5H), 8.15 (br, 1H).

Aufarbeitung

  1. temperatureto reflux under nitrogen
  2. customevaporate the toluene under reduced pressure
  3. customto form a residue
  4. filtrationFilter off catalyst
  5. concentrationconcentrate the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-106d28dc5c944e1bad71daa18b56160f
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157488B2

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