Reacción #3221

Ecuación de reacción

sodium hydroxide

2,6-dichloro-4-nitroanisole

tin(II) dichloride dihydrate

→

title compound

Rendimiento 83.7%

3,5-Dichloro-4-methoxyaniline

Rendimiento 83.7%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 3 hr
2. 2
   FiltraciónThe resulting mixture was filtered through diatomaceous earth
3. 3
   Extracciónthe filtrate was extracted with ethyl acetate
4. 4
   SecadoThe combined ethyl acetate extracts were dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated

Procedimiento

A stirred mixture of 2,6-dichloro-4-nitroanisole (4.6 g, 21 mM) and tin(II) dichloride dihydrate (23.4 g, 104 mM) in ethanol (72 mL) was refluxed for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice water which was then treated with 2N sodium hydroxide until the solution became basic. The resulting mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate. The combined ethyl acetate extracts were dried (MgSO4), filtered and concentrated to obtain (3.33 g, 83.7%) the title compound as a yellow-brown solid, mp 80°-81° C.; MS(CI): 192 (M+H).

Fuente