Acetic Acid → N2-(1-(quinolin-2-yl)azetidin-3-yl)pyridine-2,3-diamine
Reaktionsgleichung
[N+:1]([C:4]1[C:5]([NH:10][CH:11]2[CH2:14][N:13]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)[CH2:12]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.C(O)(=O)C>C(O)C.O.[Fe]>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[N:13]1[CH2:14][CH:11]([NH:10][C:5]2[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:12]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 95 °C
Versuchsvorschrift
To a solution of 3-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine (1.05 g, 3.20 mmol) in ethanol (30 mL) and water (10 mL) was added iron (448 mg, 8.0 mmol) and acetic acid (240 mg, 4.0 mmol) slowly dropwise. The mixture was heated at 95° C. until TLC analysis confirmed the absence of starting materials. The reaction mixture was filtered through a plug of CELITE™ washing with methanol. The black filtrate was concentrated in vacuo, treated with brine (40 mL) and extracted with dichloromethane (3×60 mL). The combined organic extracts were washed with water (30 mL) and brine (30 mL) and then dried over sodium sulfate. The filtrate was evaporated in vacuo to give N2-(1-(quinolin-2-yl)azetidin-3-yl)pyridine-2,3-diamine (0.744 g, 2.6 mmol, yield 80%).
Aufarbeitung
- filtrationThe reaction mixture was filtered through a plug of CELITE™
- washwashing with methanol
- concentrationThe black filtrate was concentrated in vacuo
- additiontreated with brine (40 mL)
- extractionextracted with dichloromethane (3×60 mL)
- washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
- dry with materialdried over sodium sulfate
- customThe filtrate was evaporated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-b28e388cbf574c348ff6dcbf723cd7b0
- Quelldatensatz
- uspto-grants-2015_11
- Patentnummer
- US09174992B2
Notizen zur Reaktion
Wird geladen…