4-Chloroaniline → N-(4-chlorophenyl)-4-[1-(pyridin-4-yl)ethyl]phthalazin-1-amine

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Reaction Steps

A mixture of 300 mg (1.19 mmol) rac 4-[1-(4-pyridyl)ethyl]-1 (2H)-phthalazinone, 683 mg (4.77 mmol) phosphorus pentoxide, 657 mg (4.77 mmol) triethylamine hydrochloride, and 609 mg (4.77 mmol) 4-chloroaniline is heated for 8 h to 205° C. The brown solution is taken up in dichloromethane/methanol 19:1, washed successively with sat. Na2CO3 solution, 3× with water and brine, and the organic phase (Na2O4) is washed and concentrated by evaporation. Chromatography (SiO2; ethyl acetate/CH3OH 19:1) yields the title compound: m.p.: 132-134° C.; Anal. calc. (C21H17N4Cl.½CH3OH) C 68.52%, H 5.08%, N 14.87%; found. C 68.4%, H5.0%, N 14.9%.

Provenance & Evidence