The general procedure for the synthesis of 3-methoxy-2-methylaniline from 2-methyl-3-nitroanisole is as follows (reference Example 42):
1. 9.98 g of a suspension of 5% palladium-carbon (wet) in 100 mL of ethanol was added to a solution of 30.7 g (184 mmol) of 2-methyl-3-nitroanisole in 300 mL of ethanol.
2. The reaction mixture was stirred at room temperature and under hydrogen atmosphere for 3 hours.
3. Upon completion of the reaction, the reaction solution was filtered through diatomaceous earth.
4. The filtrate was concentrated under vacuum to give 25.5 g of 3-methoxy-2-methylaniline as a light purple oil (Yield: quantitative).
Rf value: 0.38 (hexane: ethyl acetate = 2:1, v/v).
Mass spectrum (EI, m/z): 137 (M+).
1H-NMR spectrum (CDCl3, δ ppm): 2.04-2.05 (m, 3H), 3.60 (brs, 2H), 3.80 (s, 3H), 6.33-6.37 (m, 2H), 6.94-7.01 (m, 1H).
