Tetrahydrofuran → 3-(4-Nitro-pyridin-2-ylmethylene)-3H-isobenzofuran-1-one

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Reaction Steps

To a cooled solution of (4-oxo-3,4-dihydro-phthalazin-1-yl)-phosphonic acid dimethyl ester (0.202 g, 0.837 mmol) in THF (4 mL) at 10° C. was added 4-nitro-pyridine-2-carbaldehyde (0.837 mmol) under a nitrogen atmosphere. Triethylamine (0.174 mL, 1.25 mmol) was added dropwise over 10 minutes and then allowed to stir at room temperature for 18 hours. The yellow suspension was poured in water (9 mL), and the then filtered, the solid was washed with water (2×2 mL), hexane (2×2 mL) and then diethyl ether (2×2 mL) and then dried in vacuo to afford a 0.73 g of the desired products. Two peaks in LC-MS analysis, (0.13 g, 18% two steps) and required no further purification, m/z (LC-MS, ESP), RT=4.26 mins (M+H) 269, & RT=4.52 mins (M+H) 269.

Provenance & Evidence