Reacción #2383799

ord-d9b1db72bdf34a3c84da1b7fead8faf2

Ecuación de reacción

O=Cc1cc([N+](=O)[O-])ccc1F
2-fluoro-5-nitrobenzaldehyde
NCCO
ethanolamine
O=[N+]([O-])c1ccc(F)c(CNCCO)c1
crystals
Rendimiento 57.0%
O=[N+]([O-])c1ccc(F)c(CNCCO)c1
2-[(2-Fluoro-5-nitrobenzyl)amino]ethanol
Rendimiento 57.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroevaporated
  2. 2
    Extracciónextracted with methylene chloride (3×150 ml)
  3. 3
    Extracciónextracted with methylene chloride (4×200 ml)
  4. 4
    LavadoThese extracts were washed with saturated brine solution
  5. 5
    Secadodried over magnesium sulfate
  6. 6
    Otroevaporated

Procedimiento

To 2-fluoro-5-nitrobenzaldehyde (52.4 g, 0.31 mol) in absolute ethanol (500 ml) was added ethanolamine (18.93 g, 0.31 mol) and borane-pyridine complex (31.31 ml, 0.31 mol). The mixture was stirred for 48 h and then evaporated. The residue was acidified with 2.5N hydrochloric acid, extracted with methylene chloride (3×150 ml), and the extracts were discarded. The aqueous phase was basified with 25% aqueous sodium hydroxide and extracted with methylene chloride (4×200 ml). These extracts were washed with saturated brine solution, dried over magnesium sulfate and evaporated to give yellow crystals (37.67 g, 57%), m.p. 98.5-99.5° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06489322B1uspto-grants-2002_12