Tetrahydrofuran → HCID 10594477, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-amino-7-chloro-3-phenyl-2(1H)-quinolone (Example 2) (0.5 g) in 50 ml tetrahydrofuran was stirred under an atmosphere of nitrogen and treated with sodium hydride (0.3 g, 80% disp. in mineral oil). This was followed by the addition after 1 h of ethyl malonyl chloride (1.8 ml). The reaction mixture was heated at 60° C. for 14 h, cooled and partitioned between ethyl acetate and water. The organic phase was washed with water (2×) before the solvent was removed in vacuo. The residue was saponified using 4N sodium hydroxide lo (100 ml) and ultrasound. The solution was adjusted to pill using conc. HCl then extracted into ethyl acetate, dried (MgSO4) and the solvent was removed in vacuo. The residue was purified by preparative HPLC followed by recrystallisation from DMF-water to give the title compound (50 mg); mp 260° C. decomposed; δ (360 MHz, DMSO) 3.22 (2H, s, CH2CO2H), 7.22-7.76 (7H, m, aromatics), 7.87 (1H, d, 5-H, J=8.4 Hz), 9.97 (1H, s, NHCOCH2CO2H), 12.13 (1H, s, NH). Found: C, 60.29; H, 3.83; N, 7.69. C18H13N2O4Cl requires C, 60.60; H, 3.67; N, 7.85%.

Provenance & Evidence