N-bromobutanimide → 5-bromo-3-ethyl-6-methyl-1H-pyridin-2-one

A mixture of 3-ethyl-6-methyl-1H-pyridin-2-one (23.92 g, 174.4 mmol) and N-bromosuccinimide (32.67 g, 183.5 mmol) in methanol (450 ml) was stirred under nitrogen at room temperature. A thick suspension formed after some hours and was stirred at RT for a further 24 h. The reaction mixture was concentrated to one half to one third of the original volume and diluted with 200 ml of water. The mixture was cooled in an ice bath with stirring and then filtered with suction. The residue was washed with cold water and dried at 65° C. 35.93 g (95%) of 5-bromo-3-ethyl-6-methyl-1H-pyridin-2-one were obtained in the form of a beige powder.

1. customA thick suspension formed after some hours
2. stirringwas stirred at RT for a further 24 h
3. concentrationThe reaction mixture was concentrated to one half to one third of the original volume
4. additiondiluted with 200 ml of water
5. temperatureThe mixture was cooled in an ice bath
6. stirringwith stirring
7. filtrationfiltered with suction
8. washThe residue was washed with cold water
9. customdried at 65° C

ORD record

ord-c9bd2d12d9e242bbb0e6c83deb55f695

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863280B2