Reacción #11588

Ecuación de reacción

3-[(4-hydroxy-phenylamino)-methylene]-1,3-dihydro-indol-2-one

potassium carbonate

1-bromo-4-chlorobutane

→

compound

Rendimiento 47.0%

3-{[4-(4-Chloro-butoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one

Rendimiento 47.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture is partitioned between EtOAc and water
2. 2
   OtroThe organic layer is collected
3. 3
   Lavadowashed sequentially with H2O (1×), saturated aqueous NaHCO3 solution (1×), and brine (1×)
4. 4
   OtroThe organic phase is dried
5. 5
   Concentraciónconcentrated
6. 6
   Otroto give a solid
7. 7
   OtroThe solid is triturated with MeOH
8. 8
   Filtracióncollected by filtration

Procedimiento

A solution of 3-[(4-hydroxy-phenylamino)-methylene]-1,3-dihydro-indol-2-one (0.945 g, 3.75 mmol) in 20 mL DMF is treated with potassium carbonate (777 mg, 1.5 equiv.) and 1-bromo-4-chlorobutane (1.1 equiv.). The reaction mixture is heated to 40° C. for 3 h. The reaction mixture is partitioned between EtOAc and water. The organic layer is collected and washed sequentially with H2O (1×), saturated aqueous NaHCO3 solution (1×), and brine (1×). The organic phase is dried and concentrated to give a solid. The solid is triturated with MeOH and collected by filtration to give the named compound as yellow solid (600 mg, 47%).

Fuente