Potassium Carbonate → 3-Methoxy-4-methylaniline

Participants

Reaction Steps

To a solution of 2-methyl-5-nitroanisole (11.56 g, 69.2 mmol) in a mixture of ethyl acetate (200 mL) and ethanol (70 mL) was added portionwise tin (II) chloride dihydrate (109 g, 0.483 mol) and the mixture was stirred at room temperature overnight. The reaction mixture was basified with aq. K2CO3 and filtered over celite. The layers were separated. The aqueous layer was further extracted with ethyl acetate and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated to give 8.02 g of 3-methoxy-4-methyl-aniline (86% yield). 1H NMR (300 MHz; CDCl3): 2.09 (s, 3 H), 3.76 (s, 3 H), 4.01 (br s, 1 H), 6.20 (m, 2 H), 6.90 (d, J=8.4 Hz, 1 H).

Provenance & Evidence