1-Chloro-4-(4-pyridinylmethyl)phthalazine → HCID 22741993, compound

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Reaction Steps

To 262 mg (1.05 mmol) decyloxyaniline (Salor) in 5 ml ethanol, 0.26 ml HCl/dioxane 4N is added, the mixture stirred for ≈3 min, and then 256 mg (1.00 mmol) 1-chloro-4-(4-pyridyl-methyl)phthalazine (Example 67A.1) is added. After 2 h boiling under reflux, the mixture is cooled and concentrated by evaporation. The residue is stirred with 6 ml NH3 solution (10% in water: or 10 ml sat. NaHCO3 solution) and 15 ml dichloromethane/methanol 50:1 for 30 min. The aqueous phase is then separated off and extracted again with dichloromethane. The organic phase is dried (Na2SO4) and concentrated by evaporation. Crystallization [possibly after chromatography on SiO2 (ethyl acetate/CH3OH, 19:1)] from acetonitrile (or methanol) yields the title compound: m.p.: 116-119° C.; Anal. calc.(C30H36N4O) C, 76.89%; H, 7.74%; N, 11.96%; found C, 76.7%; H, 7.7%; N, 11.9%; FAB MS (M+H)+=469.

Provenance & Evidence