Reacción #155344

ord-e5fb0f73a8024e808d784f64d3c305f8

Ecuación de reacción

[H][H]
hydrogen
COc1ccc(-c2c[nH]c3c(OCCOCc4ccccc4)ccc(F)c3c2=O)cc1
8-(2-benzyloxyethoxy)-5-fluoro-3-(4-methoxyphenyl)-1H-quinolin-4-one
COc1ccc(-c2c[nH]c3c(OCCO)ccc(F)c3c2=O)cc1
5-fluoro-8-(2-hydroxyethoxy)-3-(4-methoxyphenyl)-1H-quinolin-4-one
Rendimiento 105.3%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroAfter completion of the reaction
  2. 2
    Otrothe catalyst was removed
  3. 3
    Concentraciónthe mixture was concentrated under reduced pressure
  4. 4
    OtroThe residue was purified
  5. 5
    ConcentraciónThe purified material was concentrated to dryness under reduced pressure

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE045108E1uspto-grants-2014_09