p-Nitrocinnamonitrile → p-Nitrocinnamamidoxime

HRID 596775Notes

Reaction equation

HRID 596775 reaction equation
[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]

Participants

5

Reactant 3

HCID 34056p-NitrocinnamonitrileHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 54565412p-Nitrocinnamamidoxime

Reagents, catalysts & solvents 1

HCID 787HydroxylamineSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-9011015699374368ba89bd4336bedf98
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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