Hydrochloric Acid → 5-Methoxy-2-(pyridin-2-yl)aniline

Participants

Reaction Conditions

Reaction Steps

1.63 g of 2-(4-methoxy-2-nitrophenyl)pyridine was dissolved in 14 ml of ethanol, and 8 g of stannous chloride dihydrate and 5.7 ml of concentrated hydrochloric acid were added. The mixture was stirred at a bath temperature of 100° C. for 3 hours. After cooling, the reaction mixture was made alkaline with a 50% aqueous solution of sodium hydroxide and extracted with benzene. The solvent was evaporated. The resulting dark brown oil was subjected to silica gel column chromatography and the column was eluted with chloroform. As a yellow oil, 967 mg (yield 68.2%) of 2-(2-amino-4-methoxyphenyl)pyridine was obtained.

Provenance & Evidence