Thionyl Chloride → 6-Chloro-N-methoxy-N-methylnicotinamide

A mixture of 6-chloronicotinic acid (80 g, 0.48 mmol) and thionyl chloride (400 ml) was heated under reflux for 3 hours. The cooled mixture was evaporated under reduced pressure and the residue was dissolved in dichloromethane (600 ml). N,O-dimethylhydroxylamine hydrochloride (54.6 g, 0.56 mmol) was added to the mixture which was then cooled in ice and treated with triethylamine (200 ml). The suspension was stirred for 1 hour at room temperature and was then filtered. The filtrate was washed with dilute sodium hydroxide solution (2N, 300 ml), brine (200 ml) and dried (MgSO4). The solution was evaporated under reduced pressure then distilled to give the title compound, (90 g), b.p. 106°-110° C. at 0.5 mm.

1. temperaturewas heated
2. temperatureunder reflux for 3 hours
3. customThe cooled mixture was evaporated under reduced pressure
4. dissolutionthe residue was dissolved in dichloromethane (600 ml)
5. temperaturewas then cooled in ice
6. filtrationwas then filtered
7. washThe filtrate was washed with dilute sodium hydroxide solution (2N, 300 ml), brine (200 ml)
8. dry with materialdried (MgSO4)
9. customThe solution was evaporated under reduced pressure
10. distillationthen distilled

ORD record

ord-be3d4bde47854e01868105db740421b2

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05541203