Reaction #155344

Reaction equation

hydrogen

8-(2-benzyloxyethoxy)-5-fluoro-3-(4-methoxyphenyl)-1H-quinolin-4-one

→

5-fluoro-8-(2-hydroxyethoxy)-3-(4-methoxyphenyl)-1H-quinolin-4-one

Yield 105.3%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherAfter completion of the reaction
2. 2
   Otherthe catalyst was removed
3. 3
   Concentrationthe mixture was concentrated under reduced pressure
4. 4
   OtherThe residue was purified
5. 5
   ConcentrationThe purified material was concentrated to dryness under reduced pressure

Procedure

20% palladium hydroxide/carbon (5.0 g) was added to an ethanol solution (50 ml) of 8-(2-benzyloxyethoxy)-5-fluoro-3-(4-methoxyphenyl)-1H-quinolin-4-one (6.3 g, 15.0 mmol), followed by hydrogen substitution. The mixture was stirred at room temperature for 4 hours. After completion of the reaction, the catalyst was removed and the mixture was concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=100:0→20:1). The purified material was concentrated to dryness under reduced pressure, giving a pale yellow powder of 5-fluoro-8-(2-hydroxyethoxy)-3-(4-methoxyphenyl)-1H-quinolin-4-one (5.2 g, yield: 99%).

Source