39977-95-2

944401-87-0

881668-93-5

87199-83-5

A mixture of 5-methoxy-3-nitroquinoline and 7-methoxy-3-nitroquinoline (780 mg, 3.82 mmol) was dissolved in ethyl acetate (75 mL) and the reaction mixture was purged with nitrogen for several minutes. Subsequently, 10% palladium/carbon catalyst (54 mg) was added and a hydrogen gas balloon was connected to the reaction flask. The reaction mixture was stirred overnight at room temperature under hydrogen atmosphere. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (100% ethyl acetate) to isolate two isomers: 5-methoxyquinolin-3-amine and 7-methoxyquinolin-3-amine. The final target product 5-methoxyquinolin-3-amine (80 mg, 12% yield) was obtained as a yellow powder. Its structure was confirmed by 1H NMR (CD3OD): δ 8.40 (d, 1H), 7.69 (d, 1H), 7.40 (d, 1H), 7.30 (t, 1H), 6.85 (d, 1H).LC/MS analysis showed that the molecular ion peak of the target isomer (m/z): 175.0 (MH+), with a retention time (Rt) of 1.54 min; the non molecular ion peak (m/z) of the target isomer: 175.0 (MH+) with a retention time (Rt) of 1.53 min.