Methyl 2-(3,4-dimethoxyphenyl)ethanimidate--hydrogen chloride (1/1) → Hydrochloric Acid

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Reaction Steps

A mixture of methyl-(3,4dimethoxyphenyl)-acetimidate hydrochloride (2.5 g; 10 mmol) and 2,3-diamiinobenzophenone (2.1 g; 10 mmol) in methanol (70 mL) was stirred at ambient temperature for 72 hours. The reaction mixture was concentrated to dryness, and H2O was added. The solid (2.3 g) was subjected to flash chromatography on silica gel (CH2Cl2/MeOH; 9:1) to afford a gummy material. This was dissolved in diethyl ether, and Ether-HCl was added to obtain the title compound as a buff solid, hydrochloride, penta-hydrate (250 mg), m.p. 172-175° C. Anal. Calcd. for C23H20N2O3HCl.5H2O: C, 66.97; H, 5.23; N, 6.79. Found: C, 67.11, H, 4.84; N, 6.77. Mass Spectrum: (EI; M+) m/z 372. 1H-NMR (D)MSO-d6; 400 MHz) δ8.0 (s, 1H) 7.84-7.9 (m, 2H), 7.68-7.77 (m, 3H), 7.55-7.61 (m, 2H), 7.2 (s, 1H), 6.93-7.01 (m, 2H), 4.42 (s, 2H), 3.79 (s, 3H), 3.77 ppm (s, 3H).

Provenance & Evidence