Acetone → 7-(4-Chlorobutoxy)-1,2,3,4-tetrahydroquinolin-2-one

HRID 241591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241591
Br[CH2:2][CH2:3][CH2:4][CH2:5][Cl:6].C(=O)([O-])[O-].[K+].[K+].[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][C:20](=[O:24])[NH:21]2)=[CH:16][CH:15]=1.CC(C)=O>CCCCCC>[Cl:6][CH2:5][CH2:4][CH2:3][CH2:2][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][C:20](=[O:24])[NH:21]2)=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Produkt 1

HCID 104674677-(4-Chlorobutoxy)-1,2,3,4-tetrahydroquinolin-2-oneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

1-bromo-4-chloro-butane (3.4 g, 20 mmol), anhydrous potassium carbonate powder (4.14 g, 30 mmol) and 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (1.63 g, 10 mmol) are added to 10 ml of acetone and reflux for 24 hours. The reaction solution is evaporated to dryness and dispersed with 20 ml of dichloromethane and 20 ml of water respectively. The organic layer is extracted with water (20 ml×2) and saturated saline (20 ml) successively, dried over anhydrous magnesium sulfate, and evaporated to dryness to obtain a light yellow powder. The powder is slurried in n-hexane (20 ml×3), filtered, and dried to obtain 1.98 g of 7-(4-chlorobutoxy)-3,4-dihydro-2(1H)-quinolinone, with a yield of 78%.

Aufarbeitung

  1. temperaturereflux for 24 hours
  2. customThe reaction solution is evaporated to dryness
  3. additiondispersed with 20 ml of dichloromethane and 20 ml of water respectively
  4. extractionThe organic layer is extracted with water (20 ml×2) and saturated saline (20 ml) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customto obtain a light yellow powder
  8. filtrationfiltered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ad3be813142049258aee38d0061ea6de
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653069B2

Notizen zur Reaktion

Wird geladen…