Hydroxyamine hydrochloride → (NZ)-N-[[3-fluoro-4-(4-methyl-3-pyridinyl)-2-pyridinyl]-phenylmethylidene]hydroxylamine

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Reaction Steps

A solution of (3′-fluoro-4-methyl-3,4′-bipyridin-2′-yl)(phenyl)methanone (0.025 g, 0.086 mmol) and hydroxylamine hydrochloride (0.040 g, 0.582 mmol) in pyridine (Volume: 0.428 ml) was refluxed for 2.5 hr, allowed to cool to room temperature, and then concentrated in vacuo. The crude material was dissolved in a minimal amount of CH2Cl2 to be chromatographed (required a few drops of MeOH). Purification of the crude material by silica gel chromatography using an ISCO machine (4 g column, 18 mL/min, 80-100% EtOAc in hexanes over 10 min, tr=0.3, 1.5, 2 min) gave the title compound (23.7 mg, 0.076 mmol, 89% yield) as a yellow residue. ESI MS (M+H)+=308.2.

Provenance & Evidence