Under nitrogen atmosphere, 4-methoxy-1-methyl-3-nitrobenzene (18.0 g, 108 mmol) was dissolved in 160 mL of 1,2-dimethoxyethane (DME), followed by the addition of 10% Pd/C catalyst (0.9 g). Hydrazine hydrate (16.17 g, 323 mmol) was slowly added dropwise to the above solution. The reaction mixture was heated to reflux and stirred continuously for 4 hours. After that, 3 mL of hydrazine hydrate was added additionally and stirring was continued under reflux conditions for 2 days. Upon completion of the reaction, the mixture was cooled to room temperature and filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated under reduced pressure to remove the solvent to give the crude product 5-methoxy-2-methylaniline as a yellow oil. After further vacuum drying, the product solidified to a pale yellow solid in a yield of 14.8 g (100% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 6.94 (d, J = 7.53 Hz, 1H), 6.28 (d, J = 7.53 Hz, 1H), 6.26 (s, 1H), 3.78 (s, 3H), 3.5 (br, 1H), 2.10 (s, 3H), 1.6 (br, 1H).
