3-Methyl-2-nitroanisole → 2-Methoxy-6-methylaniline

Participants

Reaction Steps

Solid 2-nitro-3-methylanisole (20 g) is added portion to a hot (40°-60° C.) suspension of iron (30 g) in 20% acetic acid (400 ml). The mixture is heated on a steam bath for 40 min, filtered still hot and neutralized (after cooling) with 50% aqueous sodium hydroxide. The mixture is steam distilled (2 liters of water collected). The distillate is extracted with diethyl ether and the etheral solution is dried and evaporated to give an oily residue of 2-methoxy-6-methylbenzenamine: nmr (CDCl3) δ2.15 (s, 3H), 3.7 (s, 2H), 3.8 (s, 3H) and 6.7 (m, 3H).

Provenance & Evidence