Selenium Dioxide → 7-Chloroquinoline-4-carbaldehyde

HRID 1721277

Reaktionsgleichung

Reaktionsgleichung von HRID 1721277
[Se](=O)=[O:2].[Cl:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH3:15])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1>O1CCOCC1.O>[Cl:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH:15]=[O:2])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 24007Selenium DioxideHCID 1704377-Chloro-4-methylquinoline

Produkt 1

HCID 218232177-Chloroquinoline-4-carbaldehydeAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Selenium dioxide (4.52g; 40.3mmol) in a mixture of 25ml of dioxane and 6ml of water was added in a dropwise fashion to 7-chlorolepidine (6; 6.50g; 36.6mmol) in 25ml of dioxane to 65 °-75° C. The temperature was raised to 85° C. and maintained there with stirring for 6 hours. After cooling, the mixture was filtered through Celite™ and concentrated. The crude material was purified on a flash column, eluting with 10% ethyl acetate/hexane to obtain 5.24g (74%) of aldehyde 7 as a yellow solid. 1H NMR (CDCl3): δ7.68 (d, 1H); 7.79 (d, 1H); 8.19 (d, 1H); 9.01 (dd, 1H); 9.21 (m, 1H); 10.45 (s, 1H). IR (KBr): 1702, 1499, 1216, 1041, 900, 653 cm-1.

Aufarbeitung

  1. temperaturemaintained there
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through Celite™
  4. concentrationconcentrated
  5. customThe crude material was purified on a flash column
  6. washeluting with 10% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-10f5c9484f7445dbb4c0c1b2bba3aa7a
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05510338

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