Sodium Carbonate → 2-Methyl-6-phenylquinoline

Participants

Reaction Steps

2-Methyl-6-phenylquinoline was prepared from 6-Bromo-2-methylquinoline by Suzuki coupling with phenylboronic acid and tetrakis(triphenylphosphine) palladium(0) in refluxing 2-ethoxyethanol. To a solution 6-Bromo-2-methylquinoline (8.9 g; 40 mmol) in 2-ethoxyethanol (100 ml) was added tetrakis(triphenylphosphine) palladium (1 g; 0.86 mmol) and the reaction mixture was stirred at room temperature for 10 minutes. Phenylboronic acid (5 g; 41 mmol) in ethoxyethanol (50 ml) was then added followed by aqueous sodium carbonate (8.4 g; 79 mmol) in water (50 ml). The reaction mixture was magnetically stirred and refluxed for 16 h. The cooled reaction mixture was extracted with chloroform (3×100 ml), washed with brine, dried over anhydrous magnesium sulphate and solvent concentrated. The residue with the solvent was filtered through a silica gel column and the colourless solution was evaporated. The residue was triturated with petroleum spirit (30-40° C.) and recrystallised from ether to give an off white solid, 5.5 g (63%); Mp 95° C. (DSC, onset). Elemental analysis: Found C, 87.60; H, 5.98; N, 6.32; C16H13N requires C, 87.64; H, 5.98; and N, 6.39%.

Provenance & Evidence