Acetic Acid → HCID 54495250, compound

Participants

Reaction Steps

A stirred suspension of (S)-glutamine (14.6 g, 100 mL) and pyridine-2,3-dicarboxylic anhydride (14.9 g, 100 mmol) in 100 mL of acetic acid is heated at reflux for 1 hour. The resulting solution is allowed to cool. The solid which forms upon cooling is filtered and the solid washed with acetic acid and dried to afford 7.11 g (26%) of crude product. The crude product is slurried in 700 mL of refluxing ethanol, the suspension cooled, and the slurry collected by filtration and dried to afford 6.10 g (23%) of N-quinolinylglutamine, which can be alternatively named as 2-(1,3-dioxo-4-azaisoindol-2-yl)-3-carbamoylpropionic acid, as a white powder. mp 222°-226° C.; 1H NMR (dmso-d6) δ 13.25 (br s, 1 H, COOH), 9.04 (dd, 1 H, J=1.2, 4.9 Hz, pyr), 8.37 (dd, 1 H, J=1.2, 7.8 Hz, pyr), 7.85 (dd, 1 H, J=4.9, 7.8 Hz, pyr), 7.20 (s, 1 H, CONH2), 6.73 (s, 1 H, CONH2), 4.83 (dd, 1 H, J=10.2, 4.8 HZ, CHN), 2.55-1.90 (m, 4 H, CH2CH2); 13C NMR (dmso-d6) 6 1173.22, 170.21, 165.8, 165.7, 155.4, 150.9, 31.7, 128.3, 126.9, 51.5, 31.4, 24.0.

Provenance & Evidence