4-Methylbenzaldehyde → 1-Hydroxy-N,N,4-Trimethyl-2-(4-Methylphenyl)-1H-Imidazole-5-Methanamine

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To a solution of 4-methylbenzaldehyde (12.6 g, 0.105 moles) in methanol (300 ml), ammonium hydroxide (sp. gr.=0.9, 180 ml) is added, followed by 2-hydroxyimino-1-dimethylamino-3-butanone hydrochloride (17.4 g, 0.0965 moles, described in Example 1). After standing overnight the mixture is evaporated to give a residue of the title compound. The residue is dissolved in methanol and a solution of hydrogen chloride in diethyl ether is added. The solution is treated with charcoal and filtered. The filtrate is evaporated and crystallized from methanol-diethyl ether to give the dihydrochloride salt of the title compound (23.99 g), mp 222°-224° C. Two recrystallizations from the latter solvent raised the melting point to 223°-226° C.; nmr (DMSO-d6) δ 2.4(s), 2.52(s), 2.83(s), 4.6(s), 7.35(s), 8.2(s) and 12.2(broad); and anal. Calc'd. for C14H19N3O.2HCl: C, 53.00; H, 6.62; N, 13.20% and Found: C, 52.55; H, 6.72; N, 13.34%.

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