Methanol → Methyl cinnoline-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 0.64 g of oxalyl chloride in 5 ml of dry toluene was added over 5 minutes to a stirred suspension of 0.98 g of 2 in 10 ml of dry toluene, at 0° C. The resulting mixture was stirred for 20 minutes at 0° C., for 30 minutes at room temperature, and for one hour at 80° C. The mixture was cooled and added in portions over 5 minutes to a stirred ice cold mixture of 0.4 g of pyridine, 0.32 g of methanol and 10 ml of dry toluene. The resulting mixture was held overnight at room temperature, then stripped in a rotary evaporator, and the residue was chromatographed over silica gel, using 5% ethyl acetate/methylene chloride mixture as eluent, to give 4, as yellow crystals, m.p.: 57°-58° C.

Provenance & Evidence