4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one oxime → 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-amine

HRID 341836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341836
[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([C:16](=[N:21]O)[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.C(O)(=O)C.[C].[Pd]>[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([NH2:21])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 1

HCID 867535164,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one oxime

Produkt 1

HCID 158384675,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-amineAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A portion (4.9 g) of 4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one oxime obtained in Step 1 was suspended in methanol (50 mL) and acetic acid (25 mL), followed by stirring at room temperature for 18 hrs under a hydrogen atmosphere in the presence of 10% palladium-carbon (0.5 g). The insoluble matter was separated by filtration with Celite® pad and the filtrate was concentrated; thereafter, the residue was dissolved in water and the pH of the solution was adjusted to about 8 with sodium hydrogencarbonate, followed by extraction with dichloromethane. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate; the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol) to yield the titled compound as pale yellow crystals (4.0 g).

Aufarbeitung

  1. customThe insoluble matter was separated by filtration with Celite® pad
  2. concentrationthe filtrate was concentrated
  3. dissolutionthereafter, the residue was dissolved in water
  4. extractionfollowed by extraction with dichloromethane
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-40879c93102a41178bcd9e717c77e8a2
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856334

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