Reaction #2446134

Reaction equation

methyl iodide

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

potassium tert-butylate

→

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

Yield 78.0%

Solvents

DMF

HCl

DMF

Conditions

Workup

1. 1
   workup.WAITFollowing overnight
2. 2
   workup.STIRRINGstirring
3. 3
   ExtractionExtraction with ethyl acetate (2×100 mL)
4. 4
   Washby washing of the organic extracts with water and brine
5. 5
   Dryingdrying over MgSO4 and removal of the solvent in vacuo
6. 6
   Othergave a light yellow solid
7. 7
   OtherPurification by flash chromatography (hexanes/ethyl acetate, 7/3, Rf=0.21)

Procedure

To a solution of 6-bromo-3,4-dihydro-1H-quinolin-2-one (339 mg, 1.50 mmol) in 15 ml dry DMF was added potassium tert-butylate (336 mg, 3.0 mmol). After the mixture was stirred for 30 min at room temperature, a solution of methyl iodide (426 mg, 3.0 mmol) in 5 ml dry DMF was added. Following overnight stirring, the mixture was diluted with 100 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, 7/3, Rf=0.21) gave 6-bromo-1-methyl-3,4-dihydro-1H-quinolin-2-one (281 mg, 1.17 mmol, 78%) as colorless needles.

Source