Tetrahydrofuran → HCID 85549802, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of diethylnicotinamide (3.56 g, 0.02 mol) and copper(I) iodide (3.8 g, 0.02 mol) in 50 ml of tetrahydrofuran was added 3.12 g (0.02 mol) of phenylchloroformate at -20° C. After addition was complete, the mixture was stirred at -20° C. for 15 minutes. Phenylmagnesium bromide (6-9 ml of a 2.9 M solution in diethyl ether) was added to the reaction mixture in a dropwise manner. This mixture was stirred at ambient temperature overnight, and then quenched with a 20% aqueous ammonium chloride solution. Diethyl ether was added, and the organic layer was separated, washed successively with 20% aquous solution of 1:1 ammonium chloride/ammonia solution, water, 10% aqueous HCl, again with water, and finally with brine solution. The organic solution was then dried and evaporated to yield 3-[(diethylamino)carbonyl]-1(4H)-pyridinecarboxylic acid, phenyl ester as a yellow oil.

Provenance & Evidence