Reacción #1478581

Ecuación de reacción

1-fluoro-4-nitrobenzene

pyridine

4,7,10-trioxatridecane-1,13-diamine

→

expected product ( 19 )

Rendimiento 52.7%

N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)-N-(4-nitrophenyl)amine

Rendimiento 52.7%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter reaction for 24 hours
2. 2
   Temperaturathe reaction mixture was cooled
3. 3
   ExtracciónNext, the reaction mixture was extracted with dichloromethane
4. 4
   Lavadowashed twice with water
5. 5
   Secadodried over MgSO4
6. 6
   Otroevaporated under vacuum
7. 7
   OtroThe crude product, isolated in the form of a yellow oil
8. 8
   Otrowas purified on a column of silica
9. 9
   Lavadoeluting with ethyl acetate (
10. 10
    Otroto separate out the dinitro derivative), and then with methanol (
11. 11
    Otroto recover the expected mono-nitro derivative)

Procedimiento

1.41 g (0.01 mol) of 1-fluoro-4-nitrobenzene and 1.62 ml (0.02 mol) of pyridine were introduced into a three-necked flask under nitrogen. 8.75 ml (0.04 mol) of 4,7,10-trioxatridecane-1,13-diamine were added dropwise with stirring. The mixture was heated to 70° C. After reaction for 24 hours, the reaction mixture was cooled and 40 ml of distilled water were then added with vigorous stirring. Next, the reaction mixture was extracted with dichloromethane, washed twice with water, dried over MgSO4 and then evaporated under vacuum. The crude product, isolated in the form of a yellow oil comprising about 90% of expected mono-nitro derivative, was purified on a column of silica, eluting with ethyl acetate (to separate out the dinitro derivative), and then with methanol (to recover the expected mono-nitro derivative). 1.8 g of expected product (19) were obtained in the form of a dark yellow oil.

Fuente