Triphenylphosphine → 5-ethyl-9-nitro-5H-phenanthridin-6-one

HRID 968280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968280
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([N:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:23](=[O:34])[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:25]=1I)[CH3:21]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(=O)([O-])[O-].[Ag+2]>[CH2:20]([N:22]1[C:23](=[O:34])[C:24]2[C:29](=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]1=2)[CH3:21]

Komponenten

6

Edukt 2

HCID 11776TriphenylphosphineHCID 22288547N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide

Produkt 1

HCID 222885445-ethyl-9-nitro-5H-phenanthridin-6-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 178418647HCID 178418647, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Palladium acetate (826 mg, 3.68 mol) was added to a suspension of silver carbonate (10.1 g, 36.8 mmol), triphenylphosphine (1.93 g, 7.36 mmol), and N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide (7.29 g, 18.4 mmol) in acetonitrile (92 ml). The reaction mixture was heated to reflux for 30 minutes and cooled to 23° C. The mixture was filtered through a plug of celite, and the filter cake was washed with ethyl acetate (100 ml) and diethyl ether (100 ml). The combined filtrates were washed with saturated sodium chloride (100 ml), dried over anhydrous sodium sulfate, and were concentrated. The residue was purified by flash column chromatography (150 ml diethyl ether followed by 150 ml of ethyl acetate) afforded 5-ethyl-9-nitro-5H-phenanthridin-6-one I-1d (2.87 g, 58%) as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 minutes
  3. filtrationThe mixture was filtered through a plug of celite
  4. washthe filter cake was washed with ethyl acetate (100 ml) and diethyl ether (100 ml)
  5. washThe combined filtrates were washed with saturated sodium chloride (100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationwere concentrated
  8. customThe residue was purified by flash column chromatography (150 ml diethyl ether followed by 150 ml of ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a2f448999d40424ab97dd6965d58f4b6
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06958347B2

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