8-Aminoquinoline → 8-(Methylsulfonylamino)quinoline

Participants

Reaction Steps

The reaction of 5.0 g (0.0347 mole) of 8-aminoquinoline with 3.97 g (0.0347 mole) of methylsulfonyl chloride was carried out in 10 ml of pyridine at room temperature. After 2 hours from the start of the reaction, the reaction mixture was washed with water, extracted with diethyl ether, purified by column chromatography and concentrated to give 10.32 g (0.032 mole, 92%) of 8-(methylsulfonamido)quinoline. Then, 5.0 g (0.016 mole) of the 8-(methylsulfonamido)quinoline, 3.07 g (0.023 mole) of zinc chloride and 6.98 g (0.069 mole) of triethylamine were suspended in 30 ml of ethanol and allowed to react at room temperature. After 3 hours, the separated yellow powder was filtered, washed with ethanol and purified by column chromatography to give 10.48 g (90.0%) of Compound M as yellow crystals. The maximum PL wavelength of this compound in chloroform was 505 nm.

Provenance & Evidence