Reaktion #72453

Reaktionsgleichung

isopropyl bromide

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

potassium tert-butylate

→

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

Ausbeute 38.9%

Lösungsmittel

DMF

HCl

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated to 80° C
2. 2
   workup.STIRRINGAfter stirring for additional 48 h
3. 3
   Temperaturthe mixture was cooled to room temperature
4. 4
   ExtraktionExtraction with ethyl acetate (2×100 mL)
5. 5
   Waschenby washing of the organic extracts with water and brine
6. 6
   Trocknendrying over MgSO4 and removal of the solvent in vacuo
7. 7
   Sonstigegave a light yellow solid
8. 8
   SonstigePurification by flash chromatography (hexanes/ethyl acetate, 4/1, Rf=0.21)

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 isopropyl bromide (814 mg, 6.64 mmol) in 10 ml dry DMF was added and the mixture heated to 80° C. After stirring for additional 48 h, the mixture was cooled to room temperature and 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, 4/1, Rf=0.21) gave 6-bromo-1-isopropyl-3,4-dihydro-1H-quinolin-2-one (347 mg, 1.29 mmol, 33%) as pale yellow solid.

Quelle