Iodoethane → 7-Bromo-1-ethyl-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one

HRID 883064

Reaktionsgleichung

Reaktionsgleichung von HRID 883064
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[CH3:15].[OH-].[K+].[CH2:18](I)[CH3:19]>CS(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])([CH3:14])[CH2:7][C:8](=[O:12])[N:9]2[CH2:18][CH3:19])=[CH:4][C:3]=1[CH3:15]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 219664237-Bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one

Produkt 1

HCID 219664867-Bromo-1-ethyl-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-oneAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

A solution of 8.5 g of 7-bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one (31.7 mmol), prepared according to WO 03/075924, in 15 mL dry DMSO was added to a prestirred solution of crushed potassium hydroxide (3.56 g, 63.4 mmol) in 15 mL of dry DMSO, followed by addition of 7.68 mL (95.2 mmol) of ethyl iodide. The reaction was stirred overnight before quenching with 100 mL of water and extracted with dichloromethane (3×150 mL), the extracts were dried with sodium sulfate, filtered, stripped and purified via flash chromatography (5% EtOAc/hexanes) to afford 8.3 g of product (88%) as a white solid. MS (electrospray): mass calculated for C14H18BrNO, 295.06; m/z found 296, [M+H]+.

Aufarbeitung

  1. custombefore quenching with 100 mL of water
  2. extractionextracted with dichloromethane (3×150 mL)
  3. dry with materialthe extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. custompurified via flash chromatography (5% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3be33e1bec5a4f33a11bb939159fbe44
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236819B2

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