Potassium Hydroxide → 7-(Methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone

HRID 656852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656852
[I-].[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N+:11]2[CH2:14][CH:15]=[CH2:16])=[CH:6][CH:5]=1.[OH-].[K+].[O:19]1CCOCC1>O.CCOC(C)=O>[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10](=[O:19])[N:11]2[CH2:14][CH:15]=[CH2:16])=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 14797Potassium Hydroxide2×HCID 312751,4-DioxaneHCID 68811156HCID 68811156, Verbindung

Produkt 1

HCID 688097807-(Methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinoneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

7-(Methyloxy)-1-(2-propen-1-yl)quinolinium iodide (14.81 g; 45.43 mmol), KOH (11.20 g; 199.89 mmol) and K3-[Fe(CN)6] (32.78 g; 99.95 mmol) were stirred in 1:1 water: 1,4-dioxane (400 ml) at rt under Argon for 1 h. More KOH (1.1 g; 19.9 mmol) and K3-[Fe(CN)6] (3.28 g; 10.0 mmol) were added to the reaction and it was stirred under the same conditions for a further 0.5 h. EtOAc (500 ml) and water (500 ml) was then added. The layers were then separated and the combined organic layers were washed with water and then concentrated. The crude residue was then purified by column chromatography on silica gel using a 0-5% MeOH/DCM gradient to give the desired product (4.90 g; 51%).

Aufarbeitung

  1. customThe layers were then separated
  2. washthe combined organic layers were washed with water
  3. concentrationconcentrated
  4. customThe crude residue was then purified by column chromatography on silica gel using a 0-5% MeOH/DCM gradient

Quellen und Nachweise

ORD-Eintrag
ord-5c9fc23cbc054d5ab5afaa8403100b84
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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