Ammonium Hydroxide → 8-Fluoro-6-methylphenanthridine
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15](=O)[CH3:16])=[CH:4][CH:3]=1.[OH-].[NH4+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[C:4](=[C:15]([CH3:16])[N:14]=[C:9]3[C:8]=2[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:3]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
N-(4′-Fluorobiphenyl-2-yl)-acetamide (18.5 g, 80.7 mmol) was mixed with polyphosphoric acid (250 g) and then heated to 120° C. with vigorous stirring for 48 hours. The hot reaction mixture was poured onto ice and stirred vigorously until homogeneous. Concentrated ammonium hydroxide was added until the pH >9. A white precipitate formed. The mixture was filtered and the white solid was dissolved in ethyl acetate (250 mL) and filtered. The filtrate was washed with saturated, aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and reduced in vacuo to a brown solid. The solid was purified by recrystallization from ethyl acetate-hexane to afford 8-fluoro-6-methylphenanthridine as white crystals (15.9 g, 94% ), m.p. 92-93° C.
Aufarbeitung
- additionThe hot reaction mixture was poured onto ice
- stirringstirred vigorously until homogeneous
- customA white precipitate formed
- filtrationThe mixture was filtered
- dissolutionthe white solid was dissolved in ethyl acetate (250 mL)
- filtrationfiltered
- washThe filtrate was washed with saturated, aqueous sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customThe solid was purified by recrystallization from ethyl acetate-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-4b5de1a79116477981c8fa45a39bbac2
- Quelldatensatz
- uspto-grants-2008_05
- Patentnummer
- US07378427B2
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