Dimethyl malonate → HCID 178464872, compound

Participants

Reaction Steps

To a solution of 4-azido-N-ethylbenzamide (3.8 g, 20 mmol) obtained in Example 43a) in methanol (200 ml) was added dimethyl malonate (3.96 g, 30 mmol) at 0-5° C., and then 28% sodium methoxide in methanol solution (5.79 g, 30 mmol) was added. The mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated, and the residue was dissolved in water (50 ml) and adjusted to pH 2-3 with 1N hydrochloric acid. The precipitated crystals were filtered off, and the filtrate was neutralized with 6% aqueous sodium hydrogen carbonate solution. The mixture was concentrated to dryness, methanol (100 ml) was added to the residue, and the insoluble material was filtered off. The filtrate was concentrated to dryness. Ethanol (50 ml) was added to the residue and the precipitated crystals were collected by filtration, and dried to give the title compound as a white powder (2.5 g, 43%).

Provenance & Evidence