Diethyl Malonate → HCID 178470067, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-amino-5,6,7,8-tetrahydroquinolin-3-yl)(p-tolyl)methanone (0.533 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 to 60%) in dichloromethane as eluent to furnish 0.186 g (25%) of ethyl 2-hydroxy-4-(p-tolyl)-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxylate as a white solid. ESI/APCI(+): 363 (M+H). NMR 1H (DMSO-d6) (ppm): δ 12.37 (s, 1H, NH); 7.35-7.19 (m, 5H, 5×Harom.); 4.00 (q, 2H, OCH2CH3); 2.88 (m, 2H, CH2); 2.66 (m, 2H, CH2); 2.35 (s, 3H, CH3); 1.86-1.79 (m, 2H, CH2); 1.74-1.69 (m, 2H, CH2); 0.90 (t, 3H, OCH2CH3).

Provenance & Evidence