Azobisisobutyronitrile → HCID 66883812, compound

A mixture of 8-bromo-5-methylquinoline (5.4 g, 24.3 mmol), N-bromosuccinimide (5.2 g, 29.2 mmol), and 2,2′-azobis(2-methylpropionitrile) (AIBN) (0.40 g, 24.3 mmol) in carbon tetrachloride (80 mL) was heated at reflux for 3 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature and filtered, using hexane for rinsing. The filtrate was concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (50 mL), and then sodium acetate (4.0 g, 48.8 mmol) was added. The resulting mixture was stirred at 100° C. for 2 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature, diluted with water and extracted with a mixture of ethyl acetate and hexane (3:7). The organic layer was washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate as eluent to afford the title product as a pale yellow solid (4.8 g).

1. temperaturewas heated
2. temperatureat reflux for 3 h under nitrogen atmosphere
3. filtrationfiltered
4. washfor rinsing
5. concentrationThe filtrate was concentrated under reduced pressure
6. dissolutionThe residue was dissolved in N,N-dimethylformamide (50 mL)
7. temperatureThe reaction mixture was cooled to room temperature
8. extractionextracted with a mixture of ethyl acetate and hexane (3:7)
9. washThe organic layer was washed with brine
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated under reduced pressure
12. customThe crude product was purified by column chromatography on silica gel

ORD record

ord-58c1a3a14dc14a47aab5681fb191851b

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871941B2