Diethyl Malonate → HCID 178470068, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-aminoquinolin-3-yl)(p-tolyl)methanone (0.525 g; 2 mmol) and diethyl malonate (1.22 mL; 8 mmol) in ethanol (10 mL) under nitrogen atmosphere was added a solution of sodium ethoxide 21% (w/w) in ethanol (2.24 mL; 6 mmol). The mixture was stirred in a sealed tube and heated to 100° C. for 48 h. The volatiles were removed under reduced pressure and the remaining residue was purified by flash-chromatography on silica gel column using a gradient of ethyl acetate (1-60%) in dichloromethane as eluent to furnish 0.217 g (30%) of ethyl 2-hydroxy-4-p-tolylbenzo[b][1,8]naphthyridine-3-carboxylate as a bright yellow solid. ESI/APCI(+): 359 (M+H). NMR 1H (DMSO-d6) (ppm): δ 12.54 (s, 1H, NH); 8.21 (s, 1H, Harom.); 8.03 (d, 1H, Harom.); 7.93-7.80 (m, 2H, 2×Harom.); 7.51-7.46 (m, 1H, Harom.); 7.41-7.32 (m, 4H, 4×Harom.); 4.02 (q, 2H, OCH2CH3); 2.43 (s, 3H, CH3); 0.94 (t, 3H, OCH2CH3).

Provenance & Evidence