Reacción #162942

Ecuación de reacción

compound

3-(4-Nitro-phenyl)-isoxazol-5-carboxylic acid ethyl ester

NH4Cl

→

title compound

Rendimiento 75.9%

3-(4-Amino-phenyl)-isoxazol-5-carboxylic acid ethyl ester

Rendimiento 75.9%

Disolventes

EtOH

THF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   TemperaturaThe reaction mixture was cooled to 25° C.
3. 3
   Filtraciónfiltered through celite
4. 4
   Lavadowashed with EtOH
5. 5
   ConcentraciónThe filtrate was concentrated
6. 6
   OtroThe oil separated
7. 7
   Extracciónwas extracted with dichloromethane (3×20 ml)
8. 8
   LavadoThe dichloromethane layer was washed with water (2×10 ml)
9. 9
   Secadodried over anhydrous Na2SO4
10. 10
    OtroThe solvent was evaporated
11. 11
    Otrothe residue was purified by flash chromatography with EtOAc: light petroleum (1:1)

Procedimiento

To a solution of the compound of step 1 (1.0 g; 3.8 mmol) and NH4Cl (0.61 g; 11.4 mmol) in EtOH (30 ml), THF (20 ml) and water (5.0 ml), was added iron powder (0.5 g, 8.9 mmol) under vigorous stirring. The resulting reaction mixture was heated at 80° C. under stirring for 3 hours. The reaction mixture was cooled to 25° C. and filtered through celite and washed with EtOH. The filtrate was concentrated and basified with NaHCO3. The oil separated was extracted with dichloromethane (3×20 ml). The dichloromethane layer was washed with water (2×10 ml) and dried over anhydrous Na2SO4. The solvent was evaporated, and the residue was purified by flash chromatography with EtOAc: light petroleum (1:1) to give the title compound of step 2 (0.67 g; 75%). Mass (ES−), 231 (M−1); 1H NMR (DMSO-d6) δ: 1.31 (t, 3H), 4.36 (q, 2H), 5.64 (s, 2H), 6.61 (d, 2H), 7.60 (d, 2H), 7.66 (s, 1H).

Fuente