Sodium Hydroxide → 4-(2-Amino-ethoxy)-[1,10]phenanthroline-2-carbaldehyde oxime

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Reaction Steps

A solution of [2-(2-formyl-[1,10]phenanthrolin-4-yloxy)-ethyl]carbamic acid tert-butyl ester (0.52 g, 1.4 mmol) was stirred for 1 hour at room temperature in a mixture of trifluoroacetic acid (5 mL) and methylene chloride (10 mL). The solvent was removed and the residue was dried and redissolved in ethanol (5 mL). A solution of hydroxylamine hydrochloride (0.88 g, 12.7 mmol) in water (7 mL) was added followed by the addition of 10% NaOH until a white precipitate formed. The mixture was heated to reflux for 1 hour, cooled down to room temperature and the white precipitate filtered, washed with cold water and dried. The title compound was isolated as a pale solid (37.0 mg, 9%)

Provenance & Evidence