Methanol → Gentianadine

Participants

Reaction Steps

4-(2-Hydroxyethyl)nicotinonitrile (I-65b: 1.1 g) in concentrated HCl (30 mL) was refluxed overnight. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mass was concentrated under reduced pressure and the crude residue was dissolved in water. The resulting reaction mass was basified with saturated NaHCO3 solution and extracted using ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford 750 mg of the product (67.75% yield).

Provenance & Evidence