Diethyl Malonate → HCID 46916503, compound

Participants

Reaction Steps

A slurry of (3-quinoxalin-2-ylphenyl)amine (200 mg, 0.904 mmol) and dietyl malonate (1.4 mL, 9.04 mmol) was heated at 160° C. in a Dean-Stark vial (Glass Solutions) for 5 hrs. The reaction mixture was diluted with ethyl acetate (25 mL), the organic phase was washed with water (20 mL) and brine (20 mL), dried over sodium sulphate, the solvent evaporated in vacuo and the residue dissolved in DCM (2 mL). The solution was loaded on a Isolute 20 g silica gel column and purified by flash chromatography (Flash Master, 5 g Isolute Silica column, gradient 0 to 5 min hexane, then ethyl acetate up to 50% over 20 min) to afford ethyl 3-oxo-3-(3-(quinoxalin-2-yl)phenylamino)propanoate (60 mg, 20% yield). LCMS calculated for C19H17N3O3 (M+H): 336.35. found 336. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.41 (1H, br.), 9.52 (1H, s), 8.52 (1H, m), 8.15-8.10 (2H, m), 8.05-8.08 (1H, m), 7.82-7.95 (3H, m), 7.55-7.60 (1H, m), 4.16 (2H, q, J=8 Hz), 3.54 (2H, s), 1.23 (3H, t, J=8 Hz).

Provenance & Evidence