Carbon Dioxide → 3-(3-Methoxyphenyl)-1H-pyrrole-2,5-dione

Participants

Reaction Steps

A 61.5 g portion of m-anisidine in 150 ml of 12N hydrochloric acid and 150 ml of water was cooled in an ice-salt bath. A 35 g portion of sodium nitrite in 80 ml of water was added dropwise, with stirring over 1/2 hour. A solution of 48.5 g of maleimide in 400 ml of acetone was added together with 50 g of dry-ice. A 125 g portion of sodium acetate was added, followed immediately by 12.75 g of cupric chloride dihydrate. The mixture was allowed to stand 18 hours, then the solid was collected and dried. A 90 g portion of this solid and 51 g of 2,4-lutidine in 250 ml of isopropanol was heated on a steam bath for 1/2 hour, then poured into 1200 ml of water. The solid was collected, dried and then recrystallized, first from isopropanol then from ethyl acetate:ethanol, giving 29.0 g of 2-(m-methoxyphenyl)maleimide as yellow crystals.

Provenance & Evidence