Reacción #1605830

ord-f3b80fee544d44879f8071b7d28f6876

Ecuación de reacción

O=C1c2ccccc2C(=O)N1Cc1ccc(-c2ccccc2)c([N+](=O)[O-])c1
2-[(3-nitro-4-phenylphenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione
NN.O
hydrazine monohydrate
NCc1ccc(-c2ccccc2)c([N+](=O)[O-])c1
(3-nitro-4-phenylphenyl)methanamine

Disolventes

Condiciones de reacción

Temperatura
70°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe reaction solution was filtered, to the filtrate
  2. 2
    workup.ADDITIONwas added 0.6 M hydrochloric acid and ethyl acetate
  3. 3
    workup.STIRRINGthe mixture was stirred vigorously
  4. 4
    OtroThe aqueous layer was separated
  5. 5
    Extracciónextracted with ethyl acetate
  6. 6
    LavadoThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. 7
    Secadodried over anhydrous sodium sulfate
  8. 8
    Concentraciónconcentrated under reduced pressure

Procedimiento

The obtained 2-[(3-nitro-4-phenylphenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione was dissolved in ethanol (30 mL), an aqueous solution of hydrazine monohydrate (2 mL) was added thereto, and the mixture was stirred at 70° C. for 1 hour. The reaction solution was filtered, to the filtrate was added 0.6 M hydrochloric acid and ethyl acetate, and the mixture was stirred vigorously. The aqueous layer was separated and, after being neutralized with a 5M aqueous solution of sodium hydroxide, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain (3-nitro-4-phenylphenyl)methanamine as a crude material (305.5 mg)

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09072734B2uspto-grants-2015_07