Methanol → HCID 19381183, compound

Participants

Reaction Steps

To a mixture of 6-methyl-8-bromoquinoline (1.0 g), 3-nitrobenzene boronic acid (0.63 g), purchased from Lancaster Chemicals, 2M NaCO3 (1.9 mL), methanol (6.5 mL) and benzene 32 mL) was added palladium tetrakis triphenylphosphine (0.47 g) and heated to reflux for 6 hours. The progress of the reaction was monitored by thin-layer chromatography. Upon completion, the reaction mixture was cooled and the solvents removed. Ethyl acetate was added to the residue and the solution was filtered through a pad of Na2SO4. The solution was concentrated and the desired product was purified and isolated by preparative thin-layer chromatography yielding 6-methyl-8-(3-nitrophenyl)quinoline (983 mg) as a yellow oil. Characteristic analytical data are: elemental analysis [calculate (found)] C: 72.72 (72.63), H: 4.58 (4.32), and N: 10.60 (10.72).

Provenance & Evidence