Reaktionsgleichung
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10]N)([O-:3])=[O:2].Cl.O.[NH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>FC(F)(F)CO>[N+:1]([C:4]1[C:5]2[NH:10][C:17]3[CH2:18][CH2:19][NH:14][CH2:15][C:16]=3[C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 105 °C
Versuchsvorschrift
2-Nitrophenylhydrazine (3.7 g, 24.2 mmol) and 4-piperidone monohydrate hydrochloride (3.7 g, 24.2 mmol) were suspended in 2,2,2-trifluoroethanol (25 mL). The resultant mixture was heated at reflux for 2 h and then concentrated. Conc. HCl (35 mL) was added in one portion. The resultant mixture was then heated at 105° C. for 15 h, and allowed to cool to rt, after which it was poured onto ice. While vigorously stirring, a 50% NaOH solution was added portionwise over 10 min until pH 12, maintaining the internal temperature at <20° C. The solid was collected via filtration and dried at room temperature under vacuum for 18 h to afford 6-nitro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2.91 g, 55%). 1H NMR (300 MHz, DMSO) δ 11.65-11.60 (br s, 1H), 7.96 (d, J=8.1 Hz, 1H), 7.80 (d, J=7.0 Hz, 1H), 7.12 (t, J=8.0 Hz, 1H), 3.86 (s, 2H), 2.99 (br s, 2H), 2.72 (br s, 2H) ppm.
Aufarbeitung
- temperatureat reflux for 2 h
- concentrationconcentrated
- additionConc. HCl (35 mL) was added in one portion
- temperatureto cool to rt
- additionafter which it was poured onto ice
- additiona 50% NaOH solution was added portionwise over 10 min until pH 12
- temperaturemaintaining the internal temperature at <20° C
- filtrationThe solid was collected via filtration
- customdried at room temperature under vacuum for 18 h
Quellen und Nachweise
- ORD-Eintrag
- ord-489fa3607a8648d0a0499118cc574908
- Quelldatensatz
- uspto-grants-2009_09
- Patentnummer
- US07592454B2
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