Reaktion #1166465

Reaktionsgleichung

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

Ausbeute 89.0%

Lösungsmittel

EtOH

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn an oven dried 500 mL round bottom flask
2. 2
   Sonstigeequipped with a Claisen adapter, pressure
3. 3
   Temperaturreflux condenser
4. 4
   Temperaturthe dark black suspensions was heated
5. 5
   Temperaturto reflux under an argon atmosphere
6. 6
   TemperaturThe resulting brown suspension was heated
7. 7
   Temperaturat reflux for 1.5 h at which time the reaction mixture
8. 8
   FiltrationTherefore, the mixture was hot filtered through Celite
9. 9
   Waschenthe pad rinsed with absolute ethanol (50 mL)
10. 10
    SonstigeThe solvent was removed under reduced pressure
11. 11
    Sonstigethe resulting light brown oil was dried in vacuo (in the dark) for 24 h

Vorschrift

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.

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