N-Hydroxysuccinimide → 5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide

To a suspension of 5-bromonicotinic acid (5.0 g) and N-hydroxysuccinimide (4.27 g) in acetonitrile (60 ml) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (7.12 g) at room temperature, and the mixture was stirred for 30 minutes. To the reaction mixture were added N,O-dimethyl-hydroxylamine hydrochloride (2.66 g) and triethylamine (10 ml), and the mixture was stirred for 64 hours and concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=2:1) to give N-methyl-N-methoxy-5-bromopyridine-3-carboxamide (3.71 g) as pale yellow oil.

1. stirringthe mixture was stirred for 64 hours
2. concentrationconcentrated under reduced pressure
3. additionTo the residue was added water
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with saturated sodium chloride solution
6. dry with materialdried with magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was separated
9. custompurified with column chromatography (ethyl acetate/hexane=2:1)

ORD record

ord-bc39649cdf3b42d39b975509a6700349

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06172061B2