4-Chloroaniline → N-(4-chlorophenyl)-4,5-dimethyl-6-(pyridin-4-ylmethyl)pyridazin-3-amine

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Reaction Steps

A solution of 0.070 g 3-chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine and 0.153 g para-chloroaniline is heated in a sealed tube for 20 h to 130° C. After cooling to RT, the solution is concentrated by evaporation, the residue diluted with 100 ml CH2Cl2 and then extracted with 100 ml sat. aqueous NaHCO3 solution. The organic phase is dried over MgSO4, concentrated by evaporation, and the residue purified by flash chromatography (FC) on silica gel in Ch2Cl2/methanol 19/1. The title compound is obtained: m.p. 196-199° C. 1H-NMR (250 MHz, CDCl3): δ=8.45 (s, wide, 2H); 7.55 (d, 2H); 7.25 (d, 2H); 7.10 (d, 2H); 6.20 (s, wide, 1H); 4.25 (s, 2H); 2.15 (s, 3H); 2.10 (s, 3H). ES-MS 325, 327 (M+H for 35Cl and 37Cl).

Provenance & Evidence