Reacción #1166465

Ecuación de reacción

Hydrazine hydrate

1,2-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-4,5-dinitrobenzene

1,2-bis[2-[2-(2-methoxyethoxy) ethoxy]ethoxy]-4,5-dinitrobenzene

CH2Cl2 MeOH

→

1,2-diamino-bis [2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene

Rendimiento 89.0%

Disolventes

EtOH

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn an oven dried 500 mL round bottom flask
2. 2
   Otroequipped with a Claisen adapter, pressure
3. 3
   Temperaturareflux condenser
4. 4
   Temperaturathe dark black suspensions was heated
5. 5
   Temperaturato reflux under an argon atmosphere
6. 6
   TemperaturaThe resulting brown suspension was heated
7. 7
   Temperaturaat reflux for 1.5 h at which time the reaction mixture
8. 8
   FiltraciónTherefore, the mixture was hot filtered through Celite
9. 9
   Lavadothe pad rinsed with absolute ethanol (50 mL)
10. 10
    OtroThe solvent was removed under reduced pressure
11. 11
    Otrothe resulting light brown oil was dried in vacuo (in the dark) for 24 h

Procedimiento

In an oven dried 500 mL round bottom flask, equipped with a Claisen adapter, pressure equalizing dropping funnel, and reflux condenser, 1,2-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-4,5-dinitrobenzene 1E (20 g, 0.04 mol) was dissolved in absolute ethanol (200 mL). To this clear solution, 10% palladium on carbon (4 g) was added and the dark black suspensions was heated to reflux under an argon atmosphere. Hydrazine hydrate (20 mL) in EtOH (20 mL) was added dropwise over 10 min to avoid bumping. The resulting brown suspension was heated at reflux for 1.5 h at which time the reaction mixture was colorless and TLC analysis (95/5; CH2Cl2 /MeOH) displayed a low RfUV active spot corresponding to the diamine. Therefore, the mixture was hot filtered through Celite and the pad rinsed with absolute ethanol (50 mL). The solvent was removed under reduced pressure and the resulting light brown oil was dried in vacuo (in the dark) for 24 h to yield 15.55 g (89%) of 1,2-diamino-bis [2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene 1F. For 1F : FAB MS, M+ : m/e 432; HRMS, M+ : 432.2471 (calcd. for C20H36N2O8, 432.2482). This material was taken to the next step without further purification.

Fuente