Tetrahydrofuran → HCID 90031761, Verbindung
Reaktionsgleichung
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])=[CH:6][CH:5]=1)([O-])=O.C1COCC1.[NH4+].[Cl-].C([O-])(O)=O.[Na+]>[Fe].O>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])=[CH:6][CH:5]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 64 °C
Versuchsvorschrift
To a mixture of 3-((6-nitro-1H-indol-1-yl)methoxy)benzonitrile (3.0 g, 10.2 mmol), THF (80 mL) and water (40 mL) were added iron powder (2.86 g, 51.2 mmol) and NH4Cl (1.09 g, 20.4 mmol) and the mixture was stirred at 64° C. overnight. The mixture was then cooled to rt and to the resulting mixture was added saturated NaHCO3 aqueous solution. The mixture was filtered and the filtrate was extracted with EtOAc (30 mL×4). The combined organic layers were washed with brine (40 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a yellow solid (1.76 g, 65%).
Aufarbeitung
- temperatureThe mixture was then cooled to rt and to the resulting mixture
- filtrationThe mixture was filtered
- extractionthe filtrate was extracted with EtOAc (30 mL×4)
- washThe combined organic layers were washed with brine (40 mL×3)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-c815e127b0d943b78df202e6c6e475d3
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09434695B2
Notizen zur Reaktion
Wird geladen…