Ethyl Acetate → (NE)-2-methyl-N-[(8-nitroquinolin-7-yl)methylidene]propane-2-sulfinamide

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Reaction Steps

Titanium tetra-ethoxide (1.2 ml, 4.95 mmol) was added to a solution of 8-nitro-quinoline-7-carbaldehyde (Intermediate 204) (0.5 g, 2.47 mmol) and 2-methylpropane-2-sulfinamide (660 mg, 5.4 mmol) in THF (20 ml) under a nitrogen atmosphere and the mixture was heated under reflux for 17 h. The solution was cooled to room temperature and poured into rapidly stirring brine (40 ml) and stirred for 30 min. EtOAc (40 ml) was added and the mixture was filtered through Celite and washed with EtOAc (40 ml). The aqueous phase was extracted with EtOAc. The organic phases were dried (MgSO4) and concentrated in vacuo. The solid was purified by column chromatography using heptane/EtOAc (1:1) to give the title compound (577 mg, 76%). The compound could not be detected by HPLCMS therefore structure was confirmed by 1H NMR.

Provenance & Evidence