Triethylamine → 4-Chloro-N-methylpicolinamide

To a solution of methylamine hydrochloride (2.057 g, 30.5 mmol) and triethylamine (14.16 ml, 102 mmol) in DCM (30 ml) at 0° C., was added 4-chloropyridine-2-carbonyl chloride (3.575 g, 20.31 mmol) in DCM (20 ml). The resulting black suspension was allowed to reach room temperature and stirred overnight. The mixture was concentrated under reduced pressure and dissolved in ethyl acetate. Water was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (3×), the combined organic layers were washed with water (3×) and brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified with column chromatography (20-50% ethyl acetate in n-heptane) to give 2.04 gram of a yellow oil (10.64 mmol, 52%). MS (ESI) m/z=170.0 [M+1]+.

1. customto reach room temperature
2. concentrationThe mixture was concentrated under reduced pressure
3. dissolutiondissolved in ethyl acetate
4. additionWater was added
5. customthe layers were separated
6. extractionThe aqueous layer was extracted with ethyl acetate (3×)
7. washthe combined organic layers were washed with water (3×) and brine
8. dry with materialdried with Na2SO4
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified with column chromatography (20-50% ethyl acetate in n-heptane)

ORD record

ord-c01a2569c4454daeb1754f553090b0c5

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08883791B2