General procedure for the synthesis of 5-methoxy-2-(1H-pyrrol-1-yl)aniline from 1-(4-methoxy-2-nitrophenyl)-1H-pyrrole: a methanolic (10 mL) suspension of 1-(4-methoxy-2-nitrophenyl)-1H-pyrrole (3 mmol) and palladium carbon (10%, 60 mg) was stirred for 5 hours under the atmosphere of hydrogen balloon. Upon completion of the reaction, the black solid was removed by filtration and the filtrate was concentrated to afford the crude product of 5-methoxy-2-(1H-pyrrol-1-yl)aniline. The crude product was purified by fast silica gel column chromatography (eluent: ethyl acetate-hexane, gradient to 1:4) to afford the target product as a light yellow oil (97% yield).1H NMR (400 MHz, CDCl3) δ 7.13-7.09 (m, 1H), 6.83-6.82 (m, 2H), 6.40-6.37 (m, 4H), and 3.84 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 159.9, 143.4, 128.2, 122.1, 121.2, 109.2, 103.6, 101.1, 55.4.
