Phosphorus oxychloride → 1-Chloro-6-methyl-5-nitroisoquinoline
Reaktionsgleichung
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[N+:12]([O-])[CH:11]=[CH:10]2>ClCCCl>[Cl:3][C:13]1[C:14]2[C:9](=[C:8]([N+:18]([O-:20])=[O:19])[C:7]([CH3:6])=[CH:16][CH:15]=2)[CH:10]=[CH:11][N:12]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
Phosphorous oxychloride (2.15 mL, 23.0 mmol) was added dropwise to a solution of 6-methyl-5-nitroisoquinoline N-oxide (0.940 g, 4.60 mmol) in 1,2-dichloroethane (40.0 mL). The mixture was heated to 70° C. for 3 h to afford an off-white suspension. The mixture was concentrated and the residue was partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 1-chloro-6-methyl-5-nitroisoquinoline (0.880 g, 86% yield) as an off-white solid. MS (ESI, pos. ion) m/z: 223.0 [M+H]+
Aufarbeitung
- customto afford an off-white suspension
- concentrationThe mixture was concentrated
- customthe residue was partitioned between dichloromethane and water
- customThe aqueous phase was separated
- extractionextracted with dichloromethane
- washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution, brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-98839fdd95d54b03b9e0394786066959
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08557830B2
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