Tetrahydrofuran → [2-(Methylamino)pyridin-3-yl]methanol

Participants

Reaction Steps

Under a nitrogen gas stream, 14.4 g (0.38 mol) of lithium aluminum hydride was added to tetrahydrofuran (300 mL) under ice cooling, and a tetrahydrofuran (100 mL) solution of crude 2-(methylamino)nicotinic acid was added dropwise to the above mixture. The resulting mixture was stirred overnight at room temperature. Ethyl acetate was added to the reaction mixture, and 152 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 was purified by column chromatography (ethyl acetate:n-hexane=1:1 to 4:1). Thus, 9.10 g (yield: 35%) of the title compound was obtained as a pale yellow viscous product.

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