Atrolactic acid → 2-(6-Nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxaline-9-ylcarbamoyl)ethyl-(4-hydroxy)benzene

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Reaction Conditions

Reaction Steps

Hydroxyphenylpropionic acid (0.17 g, 1 mmol) and carbonyldiimidazole (0.16 g, 1 mmol) in 5 mL tetrahydrofuran were stirred at reflux for 15 min. The mixture was added to the starting amine (example 15, 0.15 g, 0.5 mmol) and heated at 60° C. for 30 min. Triethylamine (0.1 g) was added and the mixture heated an additional 5 h. The solvent was removed by rotoevaporation, and the residue suspended in tetrahydrofuran. The solid was collected by filtration and dried. CI MS m/e (M+1) 425. H-NMR (400 MHz, dmso) 1H, s, 12.1; 1H, s, 11.45; 5 Ar H, 8.0-6.6 including 1H, s, 7.65; 1H, m, 4.1; +other ring protons.

Provenance & Evidence