Reaktion #72452

Reaktionsgleichung

ethyl bromide

6-bromo-3,4-dihydro-1H-quinolin-2-one

potassium tert-butylate

→

6-bromo-1-ethyl-3,4-dihydro-1H-quinolin-2-one

Ausbeute 69.0%

Lösungsmittel

DMF

HCl

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITFollowing overnight
2. 2
   workup.STIRRINGstirring
3. 3
   ExtraktionExtraction with ethyl acetate (2×100 mL)
4. 4
   Waschenby washing of the organic extracts with water and brine
5. 5
   Trocknendrying over MgSO4 and removal of the solvent in vacuo
6. 6
   Sonstigegave a light yellow solid
7. 7
   SonstigePurification by flash chromatography (hexanes/ethyl acetate, 1/1, Rf=0.52)

Vorschrift

To a solution of 6-bromo-3,4-dihydro-1H-quinolin-2-one (750 mg, 3.32 mmol) in 20 ml dry DMF was added potassium tert-butylate (804 mg, 6.64 mmol). After the mixture was stirred for 30 min at room temperature, a solution of ethyl bromide (724 mg, 6.64 mmol) in 10 ml dry DMF was added. Following overnight stirring, the mixture was diluted with 150 ml 1 N HCl. Extraction with ethyl acetate (2×100 mL) followed by washing of the organic extracts with water and brine, drying over MgSO4 and removal of the solvent in vacuo gave a light yellow solid. Purification by flash chromatography (hexanes/ethyl acetate, 1/1, Rf=0.52) gave 6-bromo-1-ethyl-3,4-dihydro-1H-quinolin-2-one (583 mg, 2.29 mmol, 59%) as a colorless solid.

Quelle