General procedure for the synthesis of 4-methoxy-o-phenylenediamine from 4-methoxy-2-nitroaniline: 360 mg (2.14 mmol) of 4-methoxy-2-nitroaniline was placed in a hydrogenation reactor and 65 mL of ethanol was added. Subsequently, a small amount of 10% palladium/activated carbon catalyst was added and the reaction mixture was hydrogenated at room temperature under 50 Psi hydrogen pressure for 24 hours. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated on a rotary evaporator to afford 4-methoxyphthalimide (294 mg, 2.12 mmol, 99% yield) as a dark purple oil. The product was characterized by 1HNMR (CDCl3): δ 6.64 (d, J = 8.7 Hz, 1H), 6.35-6.30 (m, 1H), 6.26 (d, J = 8.7 Hz, 1H), 3.52 (s br, 2H), 3.07 (s br, 2H).
