反应详情

A mixture of 4-methoxy-1,2-phenylenediamine dihydrochloride (1.55 g; 7.3 mmol) and methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride (1.9 g; 7.3 mmol) in methanol (50 mL) was stirred at ambient temperature for 72 hours. The methanol was concentrated to 25 mL. A yellow solid was separated by filtration. The solid was suspended in MeOH (10 mL), and treated with hydrogen chloride. The precipitate that formed was collected to obtain 515 mg (21% yield) of the title compound as a mono-hydrochloride, hydrate, yellow solid, m.p. 246-249° C. Anal. Calcd. for C18H18N2O3HCl. H2O: C, 61.72, H, 5.20; N, 7.79. Found: C, 61.61; H, 5.37; N, 7.84 . Mass spectrum: (EI; M+) m/z 310. 1H-NMR (DMSO-d6; 400 MHz) δ14.8 (broad s,1H), 8.3-8.5(d,1H), 7.62-7.63 (d, 1H), 7.3 (d,1H), 7.21-7.23 (dd 1H), 7.2 (d, 2H), 7.07-7.16(m, 3H), 3.86-3.88 (d, 6H), 3.82-3.84 ppm (s, 3H).

1. concentrationThe methanol was concentrated to 25 mL
2. customA yellow solid was separated by filtration
3. additiontreated with hydrogen chloride
4. customThe precipitate that formed
5. customwas collected