Reaktion #719692

Reaktionsgleichung

NaHCO3

N,N-dimethyl-2-[4-[(1E,6E)-7-[4-(2-morpholinoethoxy)phenyl]-3,5-dioxo-hepta-1,6-dienyl]phenoxy]acetamide

hydrazine dihydrochloride

methanol

→

title compound

Ausbeute 66.0%

N,N-dimethyl-2-[4-[(E)-2-[3-[(E)-2-[4-(2-morpholinoethoxy)phenyl]vinyl]-1H-pyrazol-5-yl]vinyl]phenoxy]acetamide

Ausbeute 66.0%

Lösungsmittel

AcOEt

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool
2. 2
   Sonstigethe organic layer was separated
3. 3
   WaschenThe obtained organic layer was washed with saturated brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (CHCl3/methanol system)

Vorschrift

To 2.70 g of N,N-dimethyl-2-[4-[(1E,6E)-7-[4-(2-morpholinoethoxy)phenyl]-3,5-dioxo-hepta-1,6-dienyl]phenoxy]acetamide were added 2.80 g of hydrazine dihydrochloride and 54 mL of methanol, and the mixture was stirred at 40° C. overnight. The reaction mixture was allowed to stand to cool, and poured into 200 mL of a saturated aqueous NaHCO3 solution. To this, 600 mL of AcOEt was added, and the organic layer was separated. The obtained organic layer was washed with saturated brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (CHCl3/methanol system) to give 1.76 g of the title compound (66% yield).

Quelle