Réaction #3221

Équation de réaction

sodium hydroxide

2,6-dichloro-4-nitroanisole

tin(II) dichloride dihydrate

→

title compound

Rendement 83.7%

3,5-Dichloro-4-methoxyaniline

Rendement 83.7%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurewas refluxed for 3 hr
2. 2
   FiltrationThe resulting mixture was filtered through diatomaceous earth
3. 3
   Extractionthe filtrate was extracted with ethyl acetate
4. 4
   SéchageThe combined ethyl acetate extracts were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Mode opératoire

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).

Source