Water → 1-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde

HRID 1590071

Reaktionsgleichung

Reaktionsgleichung von HRID 1590071
[H-].[Na+].[O:3]=[C:4]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1.[CH3:16]I.O>CN(C)C=O>[CH3:16][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[C:13]([CH:14]=[O:15])[C:4]1=[O:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5893342-Hydroxyquinoline-3-carbaldehyde

Produkt 1

HCID 49146281-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehydeAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (55% w/w suspension in oil; 0.268 g) was added portionwise to a stirred suspension of 1,2-dihydro-2-oxoquinoline-3-carbaldehyde (1 g) in dimethylformamide (10 ml) which had been cooled in an ice bath. The mixture was allowed to warm to ambient temperature and was then heated to 60° C. for 1 hour. The mixture was recooled in an ice bath and methyl iodide (0.41 ml) was added. Dimethylformamide (50 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was poured into water (50 ml) and extracted with methylene chloride (3×50 ml). The combined extracts were washed with water (50 ml) and evaporated. The residue was triturated under diethyl ether to give 1,2-dihydro-1-methyl-2-oxoquinoline-3-carbaldehyde as a pale yellow solid (0.81 g, 74%).

Aufarbeitung

  1. temperaturehad been cooled in an ice bath
  2. temperaturewas then heated to 60° C. for 1 hour
  3. customThe mixture was recooled in an ice bath
  4. extractionextracted with methylene chloride (3×50 ml)
  5. washThe combined extracts were washed with water (50 ml)
  6. customevaporated
  7. customThe residue was triturated under diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f2591202fc6a4882afa30693fac9eceb
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05202326

Verknüpfte Notizen

Wird geladen…