Aluminium lithium hydride → 5-Ethyl-5,6-dihydro-phenanthridin-9-ylamine

HRID 968283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968283
[CH2:1]([N:3]1[C:16](=O)[C:15]2[C:10](=[CH:11][C:12]([N+:18]([O-])=O)=[CH:13][CH:14]=2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:3]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([NH2:18])=[CH:13][CH:14]=2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2)[CH3:2]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 222885445-ethyl-9-nitro-5H-phenanthridin-6-one

Produkt 1

HCID 222885425-Ethyl-5,6-dihydro-phenanthridin-9-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A solution of 5-ethyl-9-nitro-5H-phenanthridin-6-one I-1d (250 mg, 0.93 mmol) in THF (1 ml) was added to a suspension of lithium aluminum hydride (99 mg, 2.6 mmol) in THF (5 ml). The reaction mixture was heated to reflux for 2 h and cooled to 23° C. Excess hydride was quenched by careful sequential addition of water (5 drops from a Pasteur pipet), 1N aqueous sodium hydroxide (5 drops from a Pasteur pipet), and water (15 drops from a Pasteur pipet). Insolubles were removed by filtration, and the filter cake was washed with ethyl acetate (2 5-ml portions). The combined filtrates were washed with water (10 ml) and saturated aqueous sodium chloride (10 ml). The organics were dried over anhydrous sodium sulfate and were concentrated. The residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane) to provide 5-ethyl-5,6-dihydro-phenanthridin-9-ylamine I-13a (52 mg, 25%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. customExcess hydride was quenched by careful sequential addition of water (5 drops from a Pasteur pipet), 1N aqueous sodium hydroxide (5 drops from a Pasteur pipet), and water (15 drops from a Pasteur pipet)
  4. customInsolubles were removed by filtration
  5. washthe filter cake was washed with ethyl acetate (2 5-ml portions)
  6. washThe combined filtrates were washed with water (10 ml) and saturated aqueous sodium chloride (10 ml)
  7. dry with materialThe organics were dried over anhydrous sodium sulfate
  8. concentrationwere concentrated
  9. customThe residue was purified by flash column chromatography (2% ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-80bfc75e312544be8bff9bf79c544a4f
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06958347B2

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