Ammonium Acetate → 4-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]-vinyl}-1-methylquinolinium iodide

Participants

Reaction Steps

A suspension of 4-formyl-2-methoxyphenyl β-D-galactopyranoside (1c)(0.20 g, 0.63 mmol), 1,4-dimethylquinolinium iodide (0.18 g, 0.63 mmol) and ammonium acetate (0.15 g, 1.9 mmol) in ethanol (20 ml) was heated at 60°-70° C., with stirring for 1 h when t.l.c. (chloroform-methanol, 5:4) indicated that the aldehyde had been completely converted into the almost non-mobile yellow product. The reaction mixture was cooled, and filtered to give a yellow solid which was washed sequentially with ethanol, acetone and ether to give (23c) as mustard yellow solid (0.33 g, 90%), m.p. 216°-220° C. (decomp.), [α]D -17° (c 1, DMOS)(Found: C, 48.89; H, 5.28; N, 2.36. C25H28INO7.2H2O calc.: C, 48.63; H, 5.22; N, 2.27%).

Provenance & Evidence