2-Methyl-8-hydroxyquinoline → 8-Hydroxy-2-quinolinecarboxaldehyde

8-hydroxy-2-methylquinoline (2 g, 12.4 mmol.), selenium dioxide (1.74 g, 15.8 mmol), 300 ml of pre-dried 1,4-dioxane, and 1.5 ml of water were mixed and stirred in a 1-L round bottom flask. The resulting solution was then refluxed for 24 h. The reaction was monitored until completion using TLC method. The reaction mixture was then filtered off, and the selenium metal was then washed with dichloromethane, and the combined filtrates were then evaporated off under reduced pressure. The crude product was then purified by sublimation under reduced pressure or by silica gel column chromatography to yield pure yellow needle crystal.

1. temperatureThe resulting solution was then refluxed for 24 h
2. filtrationThe reaction mixture was then filtered off
3. washthe selenium metal was then washed with dichloromethane
4. customthe combined filtrates were then evaporated off under reduced pressure
5. customThe crude product was then purified by sublimation under reduced pressure or by silica gel column chromatography
6. customto yield pure yellow needle crystal

ORD record

ord-461ea512d4c045988b4084611ea958cb

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321730B2