Hydroxylamine → HCID 54380485, compound

HRID 596786Notes

Reaction equation

HRID 596786 reaction equation
[NH2:1][OH:2].Cl.NO.C[O-].[Na+].[N+:9]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[CH:14]=[CH:15][C:16]#[N:17])([O-:11])=[O:10]>CO>[N+:9]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[CH:14]=[CH:15][C:16](=[N:1][OH:2])[NH2:17])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 41281HCID 41281, compoundHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 54380485HCID 54380485, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of hydroxylamine prepared from hydroxylamine hydrochloride (8.34 g.) in methanol (150 ml.) by neutralisation with sodium methoxide was added to o-nitrocinnamonitrile (6.96 g.) (S. Malinowski, Roczniki Chem., 1952, 26, 85) and the mixture was refluxed for 2 hr., then evaporated to ca. 15 ml. under reduced pressure. Ethyl acetate (150 ml.) was added, and the solution was extracted with 2N-hydrochloric acid (2 × 150 ml.). The acid extracts were neutralised with solid sodium hydrogen carbonate, giving a solid (3.3 g., 40%). Recrystallisation from aqueous methanol gave o-nitrocinnamamidoxime, m.p. 173°, λmax. 236, 265 nm, (ε 17150, 14700) (Found: C, 52.4; H, 4.5; N, 20.05. C9H9N3O3 requires C, 52.2; H, 4.4; N, 20.3%).

Workup

  1. temperaturethe mixture was refluxed for 2 hr
  2. custom, then evaporated to ca. 15 ml
  3. additionEthyl acetate (150 ml.) was added
  4. extractionthe solution was extracted with 2N-hydrochloric acid (2 × 150 ml.)
  5. customgiving a solid (3.3 g., 40%)
  6. customRecrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-2bf527b1a4a4455299192226ab4e6650
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

Loading…