Dimethylformamide → 2-METHYLISONICOTINALDEHYDE

A solution of n-butyllithium (1.6 M solution in hexanes, 6.32 mL, 12.6 mmol) in THF (50 mL) was cooled to −78° C. A solution of 4-bromo-2-methyl-pyridine (2.00 g, 11.6 mmol.) in anhydrous THF (5 mL) was added. The resulting mixture was stirred for 5 minutes, then anhydrous N,N dimethylformamide (3.39 g, 46.4 mmol,) was added. The solution was stirred for 90 min at −78° C. and quenched with saturated aqueous NH4Cl solution (30 mL). The reaction mixture was warmed to room temperature. The mixture was extracted with ethyl acetate (3×100 mL), and the combined organic phase was washed with brine (100 mL) and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give 2-methyl-pyridine-4-carbaldehyde. Yield: 1.20 g, (85%).

1. stirringThe solution was stirred for 90 min at −78° C.
2. customquenched with saturated aqueous NH4Cl solution (30 mL)
3. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
4. washthe combined organic phase was washed with brine (100 mL)
5. dry with materialdried over anhydrous Na2SO4
6. customThe solvent was evaporated under reduced pressure

ORD record

ord-797050f3758b48b98d989c82fda7614f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2