Methyl iodide → 3-(1-Cyanoethyl)pyridine-2-carbonitrile

To a solution of 3-(cyanomethyl)pyridine-2-carbonitrile (synthesized by the method of Synthesis 1973, 47, 530 mg, 3.70 mmol) in tetrahydrofuran (14 mL) was added dropwise a solution of 1.65 mol/L n-butyllithium in hexane (2.60 mL, 4.29 mmol) at −78° C. under argon atmosphere. The mixture was stirred at the same temperature for 30 minutes, and then thereto was added dropwise iodomethane (300 μL, 4.81 mmol) in tetrahydrofuran (7 mL). The mixture was stirred at the same temperature for 1 hour. The reaction solution was slowly warmed to room temperature, and then to the reaction solution was added water, and the mixture was extracted with ethyl acetate four times. The organic layer was combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→50:50) to give 3-(1-cyanoethyl)pyridine-2-carbonitrile (514 mg, 88%) as a yellow oil.

1. stirringThe mixture was stirred at the same temperature for 1 hour
2. extractionthe mixture was extracted with ethyl acetate four times
3. washwashed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→50:50)

ORD record

ord-43750f3c32c44bd19f03ee2b248b8bab

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987445B2