Water → 6(5H)-Phenanthridinone

HRID 2090542

Reaktionsgleichung

Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].C(=O)([O-])[O-].[Na+].[Na+].O>CC(N(C)C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:11]1[C:12]2[C:13]3[C:3](=[CH:2][CH:16]=[CH:15][CH:14]=3)[C:4](=[O:5])[NH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

Then, in a nitrogen atmosphere, 2-bromo-N-phenylbenzamide (17.3 g, 62.7 mmol), palladium acetate (0.70 g, 3.1 mmol), and sodium carbonate (13.3 g, 125 mmol) were dissolved in dimethylacetamide (300 mL), followed by stirring and heating at 160° C. for 6 hours to cause reaction. The reaction solution was cooled to room temperature and then poured into cooled water, followed by extraction with ethyl acetate. The organic layer was dried with sodium sulfate, followed by filtration. The filtrate was concentrated using a rotary evaporator. The residue was collected by filtration and then successively washed with hexane and water. Thus, 6-phenanthridinone (6.36 g, 32.6 mmol) was obtained in a yield of 52%.

Aufarbeitung

customreaction
temperatureThe reaction solution was cooled to room temperature
additionpoured
extractionfollowed by extraction with ethyl acetate
dry with materialThe organic layer was dried with sodium sulfate
filtrationfollowed by filtration
concentrationThe filtrate was concentrated
customa rotary evaporator
filtrationThe residue was collected by filtration
washsuccessively washed with hexane and water

Quellen und Nachweise

ORD-Eintrag: ord-270f6ea915b6400085148bc1cbd8360a
Quelldatensatz: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08436173B2

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