Methyl iodide → 4-Ethylpyridine-3-carbonitrile

Temperature

-78 °C

A solution of diisopropylamine (9.1 ml) in THF (50 ml) was cooled to −30° C. and an n-butyllithium hexane solution (1.61 M, 37 ml) was added. The mixture was stirred for 30 min. After cooling the reaction mixture to −78° C., a solution of 4-methylnicotinonitrile (7.01 g) in THF (50 ml) was added dropwise and the mixture was stirred for 15 min. Methyl iodide (9.1 ml) was added and the mixture was heated to −40° C., and saturated aqueous ammonium chloride solution was added. The reaction mixture was extracted with ethyl acetate and the organic layer was dried and concentrated. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=1:1) for purification to give the title compound (6.67 g) as a pale-yellow oil.

1. stirringthe mixture was stirred for 15 min
2. temperaturethe mixture was heated to −40° C.
3. extractionThe reaction mixture was extracted with ethyl acetate
4. customthe organic layer was dried
5. concentrationconcentrated
6. customThe residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=1:1) for purification

ORD record

ord-53a6525968494f1f9bf471f50eef7d00

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067537B2