Methane → 3-Methoxy-4-pyridin-2-ylaniline

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-methoxy-4-nitrophenyl)pyridine (5.4 g, 23.3 mmol), dimethyl hydrazine (14 mL, 233 mmol), charcoal (0.7 g), in methanol (200 mL) was added iron trichloride (0.075 g, 0.46 mmol), then heated at 65° C. overnight. The reaction mixture was quenched with H2O (50 mL), then extracted with EtOAc (3×50 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7) to give 3-methoxy-4-pyridin-2-ylaniline.

Provenance & Evidence