Reaction #155337

Reaction equation

Potassium carbonate

4-(2-chloroethyl)morpholine hydrochloride

N-methylpyrrolidone

5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1 H-quinolin-4-one

→

5-fluoro-3-(4-methoxyphenyl)-1-(2-morpholin-4-ylethyl)-8-propoxy-1H-quinolin-4-one

Yield 75.2%

Solvents

ethyl acetate

Water

Conditions

Workup

1. 1
   Otherfollowed by separation
2. 2
   WashThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   OtherThe residue was purified
5. 5
   ConcentrationThe purified product was concentrated under reduced pressure
6. 6
   Otherthe residue was recrystallized from ethyl acetate

Procedure

Potassium carbonate (2.1 g, 15.2 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (1.36 g, 7.31 mmol) were added to an N-methylpyrrolidone (NMP) solution (5 ml) of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1 H-quinolin-4-one (1.0 g, 3.05 mmol) and then stirred at 50 to 60° C. for 45 hours. Water and ethyl acetate were added to the reaction mixture, followed by separation. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=50:1→30:1). The purified product was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-1-(2-morpholin-4-ylethyl)-8-propoxy-1H-quinolin-4-one (1.01 g, yield: 75%).

Source