Dimethylformamide → N,N-dimethyl-2-(2-methyl-4-pyridyl)ethenamine

n-Butyl lithium in hexane (1.6 M, 35 ml, 56 mmol) was added dropwise to a solution of 2,4-lutidine (5.0 g, 46 mmol) in tetrahydrofuran (50 ml) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. Successively, diethylamine (5.1 g, 69 mmol) was added to the mixture, and the mixture was stirred at −78° C., and the mixture was stirred at the same temperature for 30 minutes. Furthermore, DMF (6.8 g, 93 mmol) was added to the mixture at −78° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was combined with aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (7.5 g, 99%).

1. stirringthe mixture was stirred at −78° C.
2. stirringthe mixture was stirred at the same temperature for 30 minutes
3. stirringthe mixture was stirred at the same temperature for 1 hr
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was evaporated

ORD record

ord-572e9a32e90f42de9b1aa60835ef00bf

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767665B2