Triethylamine → 6-Chloro-N-methylnicotinamide

To a stirred solution of 6-chloropyridine-3-carbonyl chloride (1.5 g, 8.52 mmol) in DCM (10 ml) at 0° C. was added methylamine hydrochloride (1.73 g, 25.5 mmol) followed by drop wise additional of triethylamine (3.55 ml, 25.5 mmol) over 10 mins. The reaction mixture was stirred at RT for 2 h then quenched by addition of brine (15 ml) and saturated Na2CO3 (5 ml). The organic layer was collected and the aqueous layer extracted with DCM (2×20 ml). The combined organic phase was washed with brine (10 ml), dried (Na2SO4), filtered and evaporated to dryness. Recrystallisation from hot DCM (˜10 ml) provided the title compound (0.995 g, 5.8 mmol, 68%) as white crystals.

1. customthen quenched by addition of brine (15 ml) and saturated Na2CO3 (5 ml)
2. customThe organic layer was collected
3. extractionthe aqueous layer extracted with DCM (2×20 ml)
4. washThe combined organic phase was washed with brine (10 ml)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customevaporated to dryness
8. customRecrystallisation from hot DCM (˜10 ml)

ORD record

ord-b234950e813346f4a9ef5d783dc1bbf1

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691804B2