HCID 178497355, compound → HCID 178490008, compound

Participants

Reaction Steps

A mixture of 2-[2-(3,4-Dimethoxyphenyl)-vinyl]-1H-benzoimidazole-5-carboxylic acid methyl ester (3.5 g; 11 mmol) in MeOH (75 mL) and 2.5N NaOH solution (7.5 mL) was refluxed for 3 hours. The reaction mixture was cooled to ambient temperature and stirred for 18 hours. The reaction mixture was concentrated to dryness. The residue was dissolved in H2O, and acidified with 2N HCl. Precipitate was collected. Recrystallization from MeOH gave 600 mg (15%) of the title compound as creamy solid, mono-hydrochloride, m.p. over 285° C. Anal. Calcd. for C18H16N2O4HCl: C, 59.92, H, 4.75; N, 7.76. Found: C, 59.62; H, 4.80; N, 7.66. Mass spectrum: (EI; M+) m/z 324. 1H-NMR (DMSO-d6; 400 MHz) δ13.5(broad s, 1H), 8.24 (d, 1H), 8.14-8.2 (d, 1H), 8.02-8.06 (dd, 1H), 7.8 (d, 1H), 7.34 (d 1H), 7.26-7.28 (dd, 1H), 7.2-7.24 (d, 1H), 7.1 (d, 1H), 3.87 (s, 3H), 3.83 ppm (s, 3H).

Provenance & Evidence