N,N'-Dimethylethylenediamine → HCID 70497117, compound

Participants

Reaction Steps

A mixture solution of 2-(5-bromo-2-methyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (1.36 g, 3.64 mmol), oxazolidin-2-one (330 mg, 3.82 mmol), copper(I) iodide (139 mg, 0.73 mmol), N,N′-dimethyl-ethane-1,2-diamine (0.157 mL, 1.46 mmol), and potassium carbonate (1.51 g, 10.9 mmol) in acetonitrile (25 mL) was stirred at 90° C. for 72 h. Then the reaction mixture was cooled to room temperature. The reaction mixture was extracted with ethyl acetate (200 mL×2), washed with saturated aqueous ammonium chloride solution (50 mL×3) and brine (50 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether) to afford 4,4-dimethyl-2-[2-methyl-5-(2-oxo-oxazolidin-3-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (0.4 g, 29%) as a white solid: MS (ESI) M+1=381.1.

Provenance & Evidence