Aniline → HCID 19026977, compound

Participants

Reaction Steps

To a solution of Compound A (1.71 g, 8.17 mmol) in methanol (80 ml) was added dropwise aniline (1.49 ml, 16.3 mmol), and the mixture was stirred at room temperature for 15 minutes. Thereto was added sodium cianoborohydride (1.62 g, 24.5 mmol) by portions. The pH of the reaction mixture was adjusted to 7 by the addition of hydrochloric acid-methanol. After being stirred for 1 hour, the reaction mixture was poured into water and basified with sodium hydrogencarbonate. The mixture was extracted with ethyl acetate, washed with water, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated to give the title compound (1) (2.82 g) in quantative yield.

Provenance & Evidence