Triethylamine → 6-Chloro-N-methoxy-N-methylnicotinamide

A suspension of 6-chloronicotinic acid (80 g, 0.5 mol) in thionyl chloride (400 ml) was heated under reflux for 3 hours to give a yellow solution. The mixture was concentrated under reduced pressure, the residue was dissolved in dichloromethane (600 ml) and treated with N,O-dimethylhydroxylamine hydrochloride (56.5 g, 0.58 mol). The suspension was cooled in ice then treated dropwise with triethylamine (220ml, 1.5 mol) and stirred for 1 hour at room temperature. The mixture was filtered, the filtrate was washed with aqueous sodium hydroxide (2N, 200 ml), dried over magnesium sulphate then concentrated under reduced pressure. The resulting liquid was distilled under reduced pressure to yield the title compound (90 g), b.p. 106-110° C. (0.5 mm Hg), which was characterised by 1H-N.M.R. spectroscopy.

1. temperaturewas heated
2. temperatureunder reflux for 3 hours
3. customto give a yellow solution
4. concentrationThe mixture was concentrated under reduced pressure
5. dissolutionthe residue was dissolved in dichloromethane (600 ml)
6. temperatureThe suspension was cooled in ice
7. filtrationThe mixture was filtered
8. washthe filtrate was washed with aqueous sodium hydroxide (2N, 200 ml)
9. dry with materialdried over magnesium sulphate
10. concentrationthen concentrated under reduced pressure
11. distillationThe resulting liquid was distilled under reduced pressure

ORD record

ord-f89c3900b5174fe1834b8624c1059129

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06015825