Anisole → Methyl 2-amino-6-chloronicotinate

Participants

Reaction Steps

To a solution of methyl 6-chloro-2-[(4-methoxybenzyl)amino]pyridine-3-carboxylate (1.0 g) in trifluoroacetic acid (5 ml) was added anisole (0.5 ml), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to azeotropic distillation with toluene. The obtained oil residue was diluted with ethyl acetate (80 ml), and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (596 mg).

Provenance & Evidence