Reacción #1997808

Ecuación de reacción

1-(5-fluoro-2-methoxy-3-methylphenyl)ethanone

ammonia

Sodium borohydride

→

1-(5-Fluoro-2-methoxy-3-methylphenyl)ethanamine

Rendimiento 82.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroresulting mixture
2. 2
   OtroThe reaction was then quenched
3. 3
   workup.ADDITIONby pouring into ammonium hydroxide (30 mL)
4. 4
   Filtraciónthe resulting inorganic precipitate was filtered off
5. 5
   Lavadowashed with ethyl acetate (2×25 mL)
6. 6
   Otrothe organic layer was separated
7. 7
   Extracciónaqueous layer was extracted with ethyl acetate (2×25 mL)
8. 8
   SecadoThe combined organic layers were dried over Na2SO4
9. 9
   Filtraciónfiltered
10. 10
    Otroevaporated

Procedimiento

To a stirred solution of 1-(5-fluoro-2-methoxy-3-methylphenyl)ethanone (1.2 g, 6.59 mmol), titanium(IV) isopropoxide (3.89 mL, 13.17 mmol) and ammonia in ethanol (16.5 mL) was stirred under nitrogen in a capped flask at ambient temperature for 6 h. Sodium borohydride (0.37 g, 9.88 mmol) was added and resulting mixture was stirred at room temperature for 3 h. The reaction was then quenched by pouring into ammonium hydroxide (30 mL), the resulting inorganic precipitate was filtered off, and washed with ethyl acetate (2×25 mL). the organic layer was separated and aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated to afford 1-(5-Fluoro-2-methoxy-3-methylphenyl)ethanamine (1.0 g, 82%): 1H NMR (400 MHz, CDCl3): δ 6.98 (dd, 1H), 6.78 (dd, 1H), 4.15 (m, 1H), 3.82 (s, 3H), 2.31 (s, 3H), 1.45 (d, 3H).

Fuente