(E)-7((5-Methyl-1H-imidazol-4-yl)methylene)-6,7-dihydroquinolin-8(5H)-one → 7-((5-Methyl-1H-imidazol-4-yl)methyl)-6,7-dihydroquinolin-8(5H)-one

HRID 252082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252082
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1/[CH:7]=[C:8]1\[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:16]=2[C:17]\1=[O:18]>CO.C(Cl)(Cl)Cl.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][CH:8]1[C:17](=[O:18])[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:10][CH2:9]1

Komponenten

5

Edukt 1

HCID 59316636(E)-7((5-Methyl-1H-imidazol-4-yl)methylene)-6,7-dihydroquinolin-8(5H)-one

Produkt 1

HCID 593166327-((5-Methyl-1H-imidazol-4-yl)methyl)-6,7-dihydroquinolin-8(5H)-oneAusbeute 5.920,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 16218511Pd barium sulfateKatalysatorHCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of (4) (1.39 g, 5.81 mmol) and Pd/BaSO4 (5 wt %, 0.47 g) in methanol and chloroform was hydrogenated at 50 psi for one hour. The reaction mixture was filtered through a bed of Celite, and washed with methanol. The solvents were removed under vacuum. The crude product was purified by chromatography on silica gel with 2 to 3% ammonia saturated methanol in dichloromethane to give 7-((5-Methyl-1H-imidazol-4-yl)methyl)-6,7-dihydroquinolin-8(5H)-one (5) as a yellow oil (0.830 g, 344 mmol, 59% yield).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a bed of Celite
  2. washwashed with methanol
  3. customThe solvents were removed under vacuum
  4. customThe crude product was purified by chromatography on silica gel with 2 to 3% ammonia saturated methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-dc34aae7478b4f8ab78445014e9409a5
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868020B2

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