Reacción #155333

Ecuación de reacción

N-Bromopropyl phthalimide

Sodium hydride

DMF

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

→

2-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1yl]propyl}isoindole-1,3-dione

Rendimiento 59.2%

Disolventes

ethyl acetate

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred at room temperature for 30 minutes and at 50° C. for 5 hours
2. 2
   Temperaturacooled
3. 3
   workup.STIRRINGby stirring for 2 hours
4. 4
   OtroThe generated insoluble matter was separated
5. 5
   Lavadowashed with water
6. 6
   Otrodried

Procedimiento

Sodium hydride (60% oil base, 800 mg, 18.3 mmol) was added to a DMF solution (25 ml) of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (5.0 g, 15.2 mmol). The mixture was stirred for 30 minutes at room temperature. N-Bromopropyl phthalimide (4.48 g, 16.7 mmol) was added to the mixture and stirred at room temperature for 30 minutes and at 50° C. for 5 hours. The reaction mixture was ice-cooled and water (20 ml) and ethyl acetate were added thereto, followed by stirring for 2 hours. The generated insoluble matter was separated, washed with water, and then dried, giving a pale yellow powder of 2-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1yl]propyl}isoindole-1,3-dione (4.63 g, yield: 59%).

Fuente