Reacción #4099

Ecuación de reacción

5-chloroindoline

1,4-dichloronitrobenzene

collidine

→

product

Rendimiento 40.0%

5-Chloro-1-(4chloro-2-nitrophenyl)indoline

Rendimiento 40.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was then cooled
2. 2
   Filtraciónfiltered from some insolubles
3. 3
   Otrothe solvent was removed in vacuo
4. 4
   Temperaturawith warming
5. 5
   OtroThe residue was partitioned between 1000 ml of dichloromethane and 500 ml of water
6. 6
   OtroThe water layer was removed
7. 7
   Lavadothe organic phase was washed twice with 2N-hydrochloric acid, once with 2N-sodium hydroxide, once more with water
8. 8
   Secadodried over Na2SO4
9. 9
   Concentraciónconcentrated to an oil
10. 10
    workup.DISSOLUTIONThis was dissolved in 170 ml of methanol
11. 11
    Otroat 0° C
12. 12
    OtroThe resultant crystals were collected
13. 13
    Lavadowashed well with cold methanol
14. 14
    Otrodried

Procedimiento

A stirred solution of 123 g (0.80 mole) of 5-chloroindoline, 134 g (0.70 mole) of 1,4-dichloronitrobenzene and 97 g (0.80 mole) of collidine in 1000 ml of dimethylformamide was heated under nitrogen at 150° C. for 48 hours. The mixture was then cooled, filtered from some insolubles, and the solvent was removed in vacuo with warming. The residue was partitioned between 1000 ml of dichloromethane and 500 ml of water. The water layer was removed and the organic phase was washed twice with 2N-hydrochloric acid, once with 2N-sodium hydroxide, once more with water, dried over Na2SO4 and concentrated to an oil weighing 230 g. This was dissolved in 170 ml of methanol and stirred at room temperature and then at 0° C. The resultant crystals were collected, washed well with cold methanol, and dried. This afforded 86.5 g (40% yield) of product, m.p. 130°-133° C. 4 g of 5-chloro-1-(4-chloro-2-nitrophenyl)indoline were recrystallized from methanol in 85% yield (overall yield: 34%); m.p. 133°-135° C.

Fuente