Hydrochloric Acid → 2-Diacetylamino-4-(4-methylphenyl)pyridine

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Reaction Steps

2-Amino-4-(4-methylphenyl)pyridine (1.27 g) was dissolved in dichloromethane (50 ml). Under ice cooling, N,N-diisopropylethylamine (1.80 ml) and acetyl chloride (735 μl) were successively added dropwise to the resulting solution. After heating to room temperature, the reaction mixture was added again with N,N-diisopropylethylamine (0.90 ml) and acetyl chloride (800 μl). The mixture was stirred for 18 hours. Methanol was added to the reaction mixture. Dilute hydrochloric acid and ethyl acetate were then added to the residue obtained by distilling off the solvent in order to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, followed by concentration. The residue was dissolved in methanol. Crystals precipitated by the addition of water were collected by filtration and dried, whereby the title compound (1.39 g, 75%) was obtained.

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