p-Nitrocinnamonitrile → p-Nitrocinnamamidoxime

HRID 596775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596775
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH2:15][OH:16].C[O-].[Na+]>NO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10](=[N:15][OH:16])[NH2:11])=[CH:12][CH:13]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 34056p-NitrocinnamonitrileHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide

Produkt 1

HCID 54565412p-Nitrocinnamamidoxime

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 787HydroxylamineLösungsmittel

Versuchsvorschrift

p-Nitrocinnamonitrile (8.12 g.) was added at 30° 35° to an anhydrous methanolic hydroxylamine solution (320 ml.) prepared by neutralising hydroxylamine hydrochloride (13.00 g.) with methanolic sodium methoxide. The solution was refluxed for 2.5 hr. and left overnight. Removal of the solvent and washing with water left the crude amidoxime, 7.07 g. (74%), m.p. 184-185° (decomp.). Recrystallisation of a sample from ethanol gave p-nitrocinnamamidoxime as yellow needles, m.p. 184° -186° , λmax. (EtOH) 235.5, 265, 344 nm, (ε 10020, 10000, 14800) (Found: C, 51.7; H, 4.7; N, 20.0. C9H9N3O3 requires C, 52.2; H, 4.4; N, 20.3%).

Aufarbeitung

  1. temperatureThe solution was refluxed for 2.5 hr
  2. customRemoval of the solvent
  3. washwashing with water
  4. waitleft the crude amidoxime, 7.07 g
  5. customRecrystallisation of a sample from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9011015699374368ba89bd4336bedf98
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04012377

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