Reacción #41762

Ecuación de reacción

dimethyl sulfate

5-fluoro-2-nitrophenylamine

trifluoroacetic anhydride

trifluoroacetamide

sodium hydroxide

→

(5-fluoro-2-nitrophenyl)methylamine

Disolventes

methylenechloride

toluene

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was quenched with saturated sodium bicarbonate solution
2. 2
   OtroThe organic layer was separated
3. 3
   Lavadowashed with water, brine
4. 4
   Otrodried
5. 5
   Otroevaporated
6. 6
   workup.STIRRINGThe biphasic mixture was stirred overnight at room temperature
7. 7
   Otroevaporated
8. 8
   Lavadowashed with water, brine
9. 9
   Otrodried
10. 10
    Otroevaporated
11. 11
    OtroThe crude was purified by column chromatography
12. 12
    Lavadoeluting with 1:1 hexanes and ethyl acetate

Procedimiento

A solution of 5-fluoro-2-nitrophenylamine (1 eq) in methylenechloride was treated with trifluoroacetic anhydride (1 eq) and stirred for 10 minutes at 0° C. The mixture was quenched with saturated sodium bicarbonate solution. The organic layer was separated and washed with water, brine, dried and evaporated. To the solution of the trifluoroacetamide (1 eq) in a mixture of toluene, acetonitrile and sodium hydroxide solution (50%) was added benzyltrimethylammonium chloride (1 eq) and dimethyl sulfate (1.2 eq). The biphasic mixture was stirred overnight at room temperature and evaporated. The mixture was taken up in ethyl acetate, washed with water, brine, dried and evaporated. The crude was purified by column chromatography eluting with 1:1 hexanes and ethyl acetate to afford (5-fluoro-2-nitrophenyl)methylamine. MS: MH+=170.

Fuente