Sodium hydride → 2-(7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazin-8-yl)pyridine 1-oxide

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Reaction Steps

To a suspension of 215 mg sodium hydride (60%) in 5 ml hexamethylphosphoramide, were added 500 mg 7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazine and 486 mg 2-chloropyridine N-oxide hydrochloride in that order, and the mixture was stirred at room temperature for six hours. The reaction mixture was poured into ice water, the resulting mixture was extracted with ethyl acetate, the extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvents were distilled off from the dried solution. The residue was subjected to column chromatography on silica gel, and the crystals obtained by elution with a 2:1 mixture of chloroform and acetone were recrystallized from 6 ml ethanol, giving 409 mg of 2-(7,8-dihydro-6,6-dimethyl-6H-[1,2,5]oxadiazolo[3,4-g][1,4]benzoxazin-8-yl)pyridine 1-oxide.

Provenance & Evidence