Dimethylformamide → HCID 22036992, compound

Participants

Reaction Conditions

Reaction Steps

8-Bromo-2-methylquinoline (0.0675 mol) was added portionwise at −70° C. under N2 flow to a mixture of a solution of butyllithium in hexane (1.6M) (0.135 mol) in tetrahydrofuran (300 ml) and diethyl ether (300 ml). The mixture was stirred for 30 minutes. A solution of DMF (0.405 mol) in tetrahydrofuran (100 ml) was added quickly. The mixture was cooled to −70° C. and stirred for 15 minutes. Ethanol (70 ml) and a NH4Cl solution 10% were added. The mixture was brought to room temperature and stirred for 15 minutes. NH4Cl was added. The mixture was extracted with EtOAc. The organic layer was separated, washed with H2O, dried (MgSO4), filtered and the solvent was evaporated. The product was used without further purification, yielding 15 g (>100%) of 2-methyl-8-quinolinecarboxaldehyde (interm. 12).

Provenance & Evidence