Methanesulfonyl chloride → Methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate

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Reaction Steps

3-Hydroxy-1-methyl-4-quinolone (30 g) was dissolved in a solution of sodium hydroxide (8 g) in water (440 ml). Activated carbon (3 g) was added and the mixture stirred at 40° for 15 minutes. The mixture was filtered and the filtrate cooled in an ice/salt bath at 0 to 5° under nitrogen. Methanesulphonyl chloride (1 5.5 ml) was added dropwise over 30 minutes and the mixture then stirred at 0 to 5° for 30 minutes. Aqueous sodium hydroxide (5M, 40 ml) was added and the mixture stirred at 0 to 5° for a further 90 minutes. The resultant solid was collected by filtration and washed with water (2×50 ml) to yield crude product. The filtrate was treated with further methanesulphonyl chloride (15.5 ml) in a similar manner to that described above to give a second crop of crude product. The two crops of crude product were combined and crystallised from industrial methylated spirit (2 1) to give the novel compound 1-methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate, m.p. 208°-209°.

Provenance & Evidence