Water → (6-Methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetaldehyde

HRID 494986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494986
[OH:1][CH:2](CO)[CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[O:14])[NH:11]2)=[CH:6][C:5]=1[O:15][CH3:16].O.I([O-])(=O)(=O)=O.[Na+].[Cl-].[Na+]>CO.O1CCCC1>[CH3:16][O:15][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:4]=1[CH2:3][CH:2]=[O:1])[NH:11][C:10](=[O:14])[CH2:9][CH2:8]2

Komponenten

7

Edukt 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 23667635Sodium periodateHCID 576827997-(2,3-Dihydroxypropyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one

Produkt 1

HCID 86601606(6-Methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetaldehydeAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

110 mg of 7-(2,3-dihydroxypropyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one was dissolved in 2 ml of methanol and 1 ml of tetrahydrofuran. Thereafter, 2 ml of water containing 0.16 g of sodium metaperiodate was added to the reaction solution while cooling on ice. The obtained mixture was stirred at room temperature for 30 minutes. A saturated sodium chloride aqueous solution was added to the reaction solution, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure, so as to obtain 87 mg of (6-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetaldehyde. This compound was directly used in the following reaction without further purification.

Aufarbeitung

  1. temperaturewhile cooling on ice
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-01c7efeeae8a4f4784777ebd24295df3
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538123B2

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