Azobisisobutyronitrile → 7-Quinolinemethanol

To a solution of 7-methylquinoline (2.86 g) in ethyl acetate (100 mL) were added N-bromosuccinimide (3.56 g) and 2,2′-azobis(isobutyronitrile) (197 mg) at room temperature, and the mixture was refluxed for 1.5 hr. The reaction mixture was allowed to cool to room temperature, and washed with water. The obtained organic layer was concentrated under reduced pressure, to the residue were added DME (200 mL), water (100 mL), and silver carbonate (27.6 g), and the mixture was stirred at room temperature for 20 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol), and then purified by NH silica gel column chromatography (ethyl acetate/hexane) to give the title compound (94 mg).

1. temperaturethe mixture was refluxed for 1.5 hr
2. washwashed with water
3. concentrationThe obtained organic layer was concentrated under reduced pressure, to the residue
4. additionwere added DME (200 mL), water (100 mL), and silver carbonate (27.6 g)
5. filtrationThe insoluble material was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
8. custompurified by NH silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-4687f1df1c0448c09811688c8d7dd398

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08883788B2