Reacción #2267080

ord-8ee4d3da0e57482d9f98599d67594ed5

Ecuación de reacción

COc1cc2c(cc1NC(C)=O)CC(C)OC2(O)c1ccc([N+](=O)[O-])cc1
22
COc1cc2c(cc1NC(C)=O)CC(C)OC2(O)c1ccc([N+](=O)[O-])cc1
6-Acetylamino-1-hydroxy-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman
CC(=O)NN
acetic hydrazide
COc1ccc(CC(C)O)c(C(=NNC(C)=O)c2ccc([N+](=O)[O-])cc2)c1NC(C)=O
desired product 23
Rendimiento 86.5%
COc1ccc(CC(C)O)c(C(=NNC(C)=O)c2ccc([N+](=O)[O-])cc2)c1NC(C)=O
2′-Acetylamino-6′-(2-hydroxypropyl)-3′-methoxy-4-nitrobenzophenone acetylhydrazone
Rendimiento 86.5%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe resulting solution was refluxed for 3 hours
  2. 2
    OtroThe solvent was removed under reduced pressure
  3. 3
    workup.ADDITIONThe residue was treated with NaHCO3
  4. 4
    Extracciónextracted with ethyl acetate
  5. 5
    LavadoThe combined organic phases were washed with brine
  6. 6
    Secadodried over Na2SO4
  7. 7
    OtroRemoval of the solvent

Procedimiento

To a solution of 22 (1.7 g) in 25 ml of ethanol was added acetic hydrazide (0.5 g) and 2 drops of concentrated HCl. The resulting solution was refluxed for 3 hours. The solvent was removed under reduced pressure. The residue was treated with NaHCO3, and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over Na2SO4. Removal of the solvent gave the desired product 23 (1.25 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06887867B2uspto-grants-2005_05