HCID 13300354, compound → HCID 20463646, compound

Participants

Reaction Steps

A solution of 4.89 g (20.9 mmoles) of Ir in 50 ml of methanol and 0.49 g of 10% palladium on charcoal are placed into a 250 ml hydrogenation flask and hydrogenated at room temperature for 30 hr. The catalyst is filtered off and the methanol evaporated in vacuo. The resulting 1,5-dimethyl-4-(4'-aminophenyl)-pyrrolidin-2-one (Is), isolated in 100% yield, is dissolved in 12 ml of 18% hydrochloric acid in a 250 ml beaker and dropwise treated with 5.23 ml of 4 N sodium nitrite solution at 0°-5° C. After 5 min at 0° C. the excess nitrite was destroyed with urea. After 10 min at 0°-5° C. the diazonium solution was added dropwise to a freshly prepared solution of CuCl (20.9 mmoles) in 8 ml of 37% hydrochloric acid at 0° C. A brown precipitate forms immediately which is warmed to 60° C. for 1 hr. Extraction with chloroform and washing with water gave 4.30 g of crude reaction product after evaporation. After filtration through 130 g of silicagel 3.80 g (81%) of It were recovered as a gum.

Provenance & Evidence