1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 19965408, compound

Participants

Reaction Steps

To a solution of 4-carboxymethoxy-7-chloro-3-phenyl-2(1H)-quinolone (Example 15, 1.83 g) in tetrahydrofuran (150 ml) under nitrogen at room temperature, was added triethylamine (3.65 ml), O-methyl hydroxylamine hydrochloride (0.96 g), 1-hydroxybenzotriazole (1.15 g) and 1-(3 dimethylaminopropyl)-3-ethyl carbodiimide (1.73 g). The reaction mixture was stirred at room temperature for 16 h, then poured into water (150 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water (1×100 ml), 1N citric acid (1×100 ml), brine (1×100 ml) and a saturated sodium hydrogen carbonate solution (1×50 ml), dried (MgSO4), filtered and the solvent was removed in vacuo to leave a solid residue. Recrystallisation from ethyl acetate gave the title compound (0.12 g). Mp 205°-207° C. m/z (CI+), 359, (m+1). 1H NMR (360 MHz, DMSO-d6) δ 3.32 (3H, s, NHOCH3), 3.93 (2H, s, OCH2CONHOCH3), 7.23 (1H, dd, J=8.63 Hz, J=1.83 Hz, 6-H), 7.36-7.45 (6H, m, Ph+8-H), 8.00 (1H, d, J=8.63 Hz, 5-H), 11.26 (1H, bs, OCH2CONHOCH3), 11.94 (1H, bs, NH). Found: C, 60.57; H, 4.26; N, 7.82; C18H15N2O4Cl requires C, 60.26; H, 4.21; N, 7.81%.

Provenance & Evidence