Azobisisobutyronitrile → 3-(Bromomethyl)quinoline

A solution of 3-methylquinoline (275 mg), N-bromosuccinimide (343 mg) and 2,2′-azobis(isobutyronitrile) (31.6 mg) in carbon tetrachloride (8.0 g) was heated under reflux for 2 hours. The mixture was cooled to room temperature, and the insoluble materials were removed by filtration, and thereto was added toluene, and the mixture was concentrated under reduced pressure. To the residue was added toluene (5 mL) to give a solution of 3-bromomethylquinoline in toluene. To a 60% suspension of NaH (70 mg) in THF (2 mL) was added dropwise a solution of the compound (300 mg) obtained in Reference Example 3-2 in THF (3 mL). To the solution was added the solution of 3-bromo-methylquinoline in toluene as mentioned above, and the mixture was stirred at 35° C. for one hour. Water was added to the reaction solution, and the organic layer was separated, dried, filtered and concentrated. The residue was purified by silica gel column chromatography to give the title compound (460 mg, 74%).

1. temperatureunder reflux for 2 hours
2. customthe insoluble materials were removed by filtration
3. additionwas added toluene
4. concentrationthe mixture was concentrated under reduced pressure
5. additionTo the residue was added toluene (5 mL)

ORD-Eintrag

ord-78bc92486e4b46c9b2a47ec349d40325

Quelldatensatz

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06759429B2