m-Toluidine → 3-(3-Methylanilino)-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine

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Reaction Steps

The compound is prepared starting from 0.070 g 3-chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine and 0.129 g meta-methylaniline in the manner described in Example 82A. After heating for 20 h to 130° C., siginificant quantities of 3-chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine are still present (TLC). For this reason, a further 0.129 g meta-methylaniline is added and heated for another 24 h to 130° C. Processing is in the manner described for Example 82A. Title compound of about 90% purity is obtained after FC in CH2Cl2/methanol 19/1; m.p. 68-90%°. 1H-NMR (250 MHz, CDCl3): δ=8.45 (d, 2H); 7.70 (t, 1H); 7.50 (s, 1H); 7.40-7.10 (m, 4H)); 6.90 (d, 1H); 6.15 (s, wide, 1H); 4.30 (s, 2H); 2.35 (s, 3H); 2.15 (s, 3H); 2.10 (s, 3H). ES-MS 305 (M+H). The starting material is prepared as follows:

Provenance & Evidence