Ethanol → HCID 178490399, Verbindung

HRID 732010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732010
Cl.[NH2:2][OH:3].[OH-:4].[Na+].CO[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12].[CH2:16](O)C>>[OH:3][NH:2][C:11](=[NH:12])[C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:4][CH3:16])[CH:9]=1

Komponenten

5

Edukt 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 737123-MethoxybenzonitrileHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 178490399HCID 178490399, VerbindungAusbeute 52 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Using the general procedure of Shine et al., J. Heterocyclic Chem. (1989) 26:125-128, hydroxylamine hydrochloride (22 ml, 5 M, 110 mmol) and sodium hydroxide (11 ml, 10 M, 110 mmol) were added to a solution of 3-methoxybenzonitrile (11.5 ml. 94 mmol) in ethanol (130 ml). The reaction mixture was then heated at reflux (80° C.) for 12 h. After the mixture was cooled, most of the solvent was removed in vacuo. The crude product was partitioned between ethyl acetate and water, washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was removed in vacuo. Flash chromatography on silica gel using 35-50% ethyl acetate in hexane yielded the title compound (8.05 g, 52%). Examples 7-9 were prepared in an analogous method to the procedure given in Example 6.

Aufarbeitung

  1. temperatureThe reaction mixture was then heated
  2. temperatureAfter the mixture was cooled, most of the solvent
  3. customwas removed in vacuo
  4. customThe crude product was partitioned between ethyl acetate and water
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-62adec1f2e434c938e6d6952b21d8723
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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