m-Chloroperbenzoic acid → 1-[1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-oxo-1,4-dihydroquinolin-7-yl]piperidine 1-oxide monohydrate

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Reaction Steps

To a stirred solution of the 4-quinolone of Example 30 (1.44 g) in dichloromethane (100 ml) was added a solution of 3-chloroperbenzoic acid (85%, 0.86 g) in dichloromethane (20 ml) and the mixture was stirred for 52 hours. A solution of 3-chloroperbenzoic acid (85%, 0.27 g) in dichloromethane (10 ml) was added and the mixture was stirred for 20 hours. Saturated aqueous sodium bicarbonate (40 ml) was added and the mixture was stirred for 45 minutes. The mixture was evaporated to dryness and the residue was extracted with dichloromethane (75 ml) for 1.5 hours using a Soxhlet apparatus. The extract was evaporated and the residue was crystallised from industrial methylated spirit:diethyl ether 4:1 to give 1-[1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-oxo-1,4-dihydroquinolin-7-yl]piperidine 1-oxide monohydrate, m.p. 163°-166°.

Provenance & Evidence