Reaktion #340499

Reaktionsgleichung

sodium bicarbonate

2-(5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile

hydrazine dihydrochloride

→

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

Ausbeute 56.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To a solution of 2-(5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.26 mg, 0.80 mmol) in ethanol (5 mL) was added hydrazine dihydrochloride (105 mg, 0.9 mmol). The resulting mixture was heated at reflux for 1 hour. It was cooled to room temperature then poured 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-(5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-methyl-1H-pyrazol-5-amine (0.15 g, 0.45 mmol, 56%) yield 1H NMR (400 MHz, d6-DMSO): 7.06-7.02 (m, 1H), 6.72-6.69 (m, 1H), 4.18-4.16 (m, 2H), 3.83-3.81 (m, 2H), 3.71-3.69 (m. 2H), 3.36-3.64 (m, 2H), 3.32 (s, 3H), 3.10 (s, 3H), 2.16 (s, 3H); MS (EI) for C16H22FN3O4: 340 (MH+).

Quelle