Tetrahydrofuran → (2-Anilinopyridin-3-yl)methanol

Participants

Reaction Steps

Under a nitrogen gas stream, 2.41 g (63.4 mmol) of lithium aluminum hydride was added to tetrahydrofuran (80 mL) under ice cooling, and a tetrahydrofuran (30 mL) solution of 6.79 g (31.7 mmol) of 2-(phenylamino)nicotinic acid was added dropwise to the above solution. The resulting mixture was stirred for 2 hours at room temperature. Ethyl acetate was added to the reaction mixture, and 25 mL of a 10% aqueous solution of sodium hydroxide was further added thereto. Insoluble materials were filtered off. The filtrate was concentrated, and the residue thus obtained was dissolved in ethyl acetate, dried, filtered, and concentrated. Thus, 6.9 g of the title compound was obtained as a yellow viscous product (yield: quantitative).

Provenance & Evidence