Reaktion #340432

Reaktionsgleichung

sodium bicarbonate

2-(3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile

hydrazine dihydrochloride

→

4-(3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-methyl-1H-pyrazol-5-amine

Ausbeute 74.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 1 hour
3. 3
   TemperaturIt was cooled
4. 4
   Extraktionthe mixture was extracted with ethyl acetate (3×10 mL)
5. 5
   ExtraktionThe combined extract
6. 6
   Waschenwas washed with aqueous sodium bicarbonate solution, brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    Sonstigeto give an oily residue which
11. 11
    Sonstigewas purified by flash chromatography (silica gel, 5% methanol-dichloromethane)

Vorschrift

To a solution of 2-(3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.57 g, 1.9 mmol) in ethanol (5 mL) was added hydrazine dihydrochloride (0.20 g, 2.2 mmol) The resulting mixture was heated at reflux for 1 hour. It was cooled, pour into a saturated sodium bicarbonate solution (10 mL), and the mixture was extracted with ethyl acetate (3×10 mL). The combined extract was washed with aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (silica gel, 5% methanol-dichloromethane) to provide 4-(3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-methyl-1H-pyrazol-5-amine (0.46 g, 1.4 mmol, 74% yield). 1H NMR (400 MHz, CDCl3): 6.96-6.92 (m, 2H), 6.87-6.84 (d, d, 1H), 4.19-4.16 (m, 4H), 3.79-3.76 (m, 4H), 3.67 (s, 2H), 3.46 (s, 3H), 3.44 (s, 3H), 2.25 (s, 3H).

Quelle