Uses
3-Methoxy-2-methylaniline is a aniline derivative used in the preparation of indoles and indazoles with potential neurochemical activity, as well as in the preparation of quinoline based antiviral agents.
Synthesis
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).
References
[1] Patent: EP1679308, 2006, A1. Location in patent: Page/Page column 56
[2] Patent: US2009/12123, 2009, A1. Location in patent: Page/Page column 14-15
[3] Patent: WO2004/103996, 2004, A1. Location in patent: Page 38-39
[4] Patent: WO2006/7700, 2006, A1. Location in patent: Page/Page column 61
[5] Patent: US2006/19905, 2006, A1. Location in patent: Page/Page column 24
