Reacción #55094

ord-34e19f4dc75d49fc88b2096e844cd957

Ecuación de reacción

Cl.NO
hydroxylamine hydrochloride
[Na]
sodium
CCOC(=O)CC(=O)Nc1cccc2ccccc12
ethyl α-naphthylcarbamoylacetate
NO
hydroxylamine
O=C(CC(=O)Nc1cccc2ccccc12)NO
α-Naphthylcarbamoylacetohydroxamic acid
Rendimiento 62.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroAfter leaving the reactants in contact for 5 hours
  2. 2
    Otrothe mixture is evaporated to dryness in vacuo
  3. 3
    Filtraciónthe solution is filtered over charcoal
  4. 4
    Otrothe product is precipitated cold with 3 N HCl
  5. 5
    Filtraciónfiltered off
  6. 6
    Lavadowashed with water
  7. 7
    OtroCRL 40,518 is obtained by recrystallisation from ethanol

Procedimiento

19.3 g (0.075 mol) of ethyl α-naphthylcarbamoylacetate are treated with a solution of hydroxylamine, prepared from 5.6 g (0.08 mol) of hydroxylamine hydrochloride and 3.68 g of sodium in 250 ml of methanol. After leaving the reactants in contact for 5 hours, the mixture is evaporated to dryness in vacuo, the residue is taken up in 400 ml of cold water, the solution is filtered over charcoal, and the product is precipitated cold with 3 N HCl, filtered off and washed with water. CRL 40,518 is obtained by recrystallisation from ethanol. Yield: 62%. Melting point: 184°-186° C. (with decomposition).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04151300uspto-grants-1979_04