Reaction #155348

Reaction equation

hydrochloric acid

ethyl (5-fluoro-4-oxo-8-propoxy-3-{4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-4H-quinolin-1-yl)acetate

→

ethyl{5-fluoro-3-[4-(2-hydroxyethoxy)phenyl]-4-oxo-8-propoxy-4H-quinolin-1-yl}acetate

Yield 89.0%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe resulting mixture was cooled to room temperature
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   workup.ADDITIONEthyl acetate and water were added to the residue
4. 4
   Otherfollowed by separation
5. 5
   WashThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified
8. 8
   ConcentrationThe purified product was concentrated under reduced pressure

Procedure

2N hydrochloric acid (6.3 ml) was added to an ethanol solution (20 ml) of ethyl (5-fluoro-4-oxo-8-propoxy-3-{4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-4H-quinolin-1-yl)acetate (840 mg, 1.59 mmol) and stirred at 50° C. for 2 hours. The resulting mixture was cooled to room temperature and then concentrated under reduced pressure. Ethyl acetate and water were added to the residue, followed by separation. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=30:1→15:1). The purified product was concentrated under reduced pressure, giving a pale yellow oily substance of ethyl{5-fluoro-3-[4-(2-hydroxyethoxy)phenyl]-4-oxo-8-propoxy-4H-quinolin-1-yl}acetate (627 mg, yield: 89%).

Source