Pyridine → 3-Methoxy-N-(3-methoxyphenyl)aniline

Participants

Reaction Steps

Cupric acetate (2.1 mmol) and pyridine (0.25 ml) were added to a vigorously stirred solution of 3-methoxyaniline (1 mmol) and 3-methoxyphenylboronic acid (2 mmol) in dry methylene chloride (3.5 ml), under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 72 h (the progress of the reaction was monitored by TLC). N-(3-Methoxyphenyl)-3-methoxyaniline (3c) was isolated by direct flash chromatography of the crude reaction mixture following preabsorption on silica gel. Yield (3c): 25%; EI-MS 229 (M+) [Lit.: Urgaonkar, S.; Verkade, J. G. J. Org. Chem. 2004, 69, 9135-9142].

Provenance & Evidence