Reaction #155322

Reaction equation

Methyl iodide

DMF

2-furan-3-yl-5-propoxy-4H-benzo[f]quinolin-1-one

sodium hydride

→

2-furan-3-yl-4-methyl-5-propoxy-4H-benzo[f]quinolin-1-one

Yield 42.0%

Solvents

ethyl acetate

Water

Conditions

Workup

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 62 hours
2. 2
   Otherthe resulting mixture was subjected to separation
3. 3
   WashThe thus-obtained organic layer was washed with water
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe residue was purified
7. 7
   ConcentrationThe purified product was concentrated under reduced pressure
8. 8
   Otherto recrystallize the residue from ethyl acetate-n-hexane

Procedure

To a DMF solution (5 ml) of 2-furan-3-yl-5-propoxy-4H-benzo[f]quinolin-1-one (300 mg, 0.94 mmol) was added sodium hydride (60% oil base, 61 mg, 1.4 mmol), and then the mixture was stirred at room temperature for 5 minutes. Methyl iodide (181 mg, 1.27 mmol) was added thereto and the resulting mixture was stirred at room temperature for 62 hours. Water and ethyl acetate were added to the reaction mixture and the resulting mixture was subjected to separation. The thus-obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:ethyl acetate=90:1→80:1). The purified product was concentrated under reduced pressure to recrystallize the residue from ethyl acetate-n-hexane, giving a pale gray powder of 2-furan-3-yl-4-methyl-5-propoxy-4H-benzo[f]quinolin-1-one (130 mg, yield: 42%).

Source