Reaktion #75509

Reaktionsgleichung

4-(3,6-dichloropyridazin-4-yl)morpholine

hydrazine hydrate

→

6-chloro-5-(morpholin-4-yl)pyridazin-3-ylhydrazine

Ausbeute 74.0%

Lösungsmittel

1,4-dioxane

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux for 20 hours
3. 3
   Sonstigewas removed in vacuo
4. 4
   SonstigeThe residue was then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate
5. 5
   ExtraktionThe aqueous layer was further extracted with dichloromethane (×2)
6. 6
   TrocknenThe combined organic extracts were dried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe residue was purified by chromatography on silica gel
10. 10
    Wascheneluting with dichloromethane/methanol/aqueous ammonia (91:8:1)

Vorschrift

A mixture of 4-(3,6-dichloropyridazin-4-yl)morpholine (5 g, 21.3 mmol) and hydrazine hydrate (7.0 ml, 141 mmol) in 1,4-dioxane (100 ml) was stirred and heated at reflux for 20 hours. Upon cooling the 1,4-dioxane was removed in vacuo. The residue was then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The aqueous layer was further extracted with dichloromethane (×2). The combined organic extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol/aqueous ammonia (91:8:1) to give 6-chloro-5-(morpholin-4-yl)pyridazin-3-ylhydrazine (3.6 g, 74%): 1H NMR (250 MHz, d6-DMSO) δ3.17-3.37 (4H, m), 3.72-3.77 (4H, m), 4.31 (2H, br s), 6.58 (1H, s), 7.97 (1H, br s); MS (ES+) m/e 230, 232 [MH+].

Quelle