Hydrazine, dihydrochloride → HCID 178496120, Verbindung

HRID 253257

Reaktionsgleichung

Reaktionsgleichung von HRID 253257
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:14]([C:17](=O)[CH3:18])[C:15]#[N:16].Cl.Cl.[NH2:22][NH2:23].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:18][C:17]1[C:14]([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH2:10][CH2:11][O:12][CH3:13])[C:3]=2[O:2][CH3:1])=[C:15]([NH2:16])[NH:23][N:22]=1

Komponenten

5

Edukt 3

HCID 17548Hydrazine, dihydrochlorideHCID 516892Sodium BicarbonateHCID 668911252-(2-(Methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile

Produkt 1

HCID 178496120HCID 178496120, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.17 g, 0.65 mmol) in ethanol (5 mL) was added hydrazine dihydrochloride (99 mg, 0.94 mmol). The resulting mixture was heated at reflux for 1 hour. It was cooled, 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 in dichloromethane) to provide 3-methyl-4-(2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-1H-pyrazol-5-amine (115 mg, 0.42 mmol, 65% yield). MS (EI) for C14H19N3O3: 278 (MH+).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperatureIt was cooled
  4. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  5. extractionThe combined extract
  6. washwas washed with aqueous sodium bicarbonate solution, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an oily residue which
  11. customwas purified by flash chromatography (silica gel, 5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0c550d25001a4059a57bc31db4a502a6
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872014B2

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