Réaction #2383799

Équation de réaction

2-fluoro-5-nitrobenzaldehyde

ethanolamine

→

crystals

Rendement 57.0%

2-[(2-Fluoro-5-nitrobenzyl)amino]ethanol

Rendement 57.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Autreevaporated
2. 2
   Extractionextracted with methylene chloride (3×150 ml)
3. 3
   Extractionextracted with methylene chloride (4×200 ml)
4. 4
   LavageThese extracts were washed with saturated brine solution
5. 5
   Séchagedried over magnesium sulfate
6. 6
   Autreevaporated

Mode opératoire

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.

Source