1-Heptyl-3-Ethoxycarbonyl-4-Methoxy-2(1H)-Quinolinone → 1-Heptyl-3-Acetyl-4-Methoxy-2(1H)-Quinolinone

Participants

Reaction Steps

A flame-dried 50 ml round bottomed flask was charged with copper (I) iodide (909 rag, 4.78 mmole) and anhydrous THF (20 mL). Methyl lithium (halide-free, 1.4M, 7.2 mL, 10.1 mmole) was added to the white CuI suspension at -78° C. After 0.5 hour the product from step (1) (430 mg. 1.25 mmole) was added drop-wise as a solution in THF (10 mL) to the solution of dimethyllithiocuprate. After 3 hours, the reaction was quenched with saturated ammonium chloride. The product was isolated by acidification of the reaction to pH 5, and extraction (3×) with ethyl acetate. Final purification on Silica-Gel 60 (4:1 hexane:ethyl acetate eluent) gave the title compound in 75% yield. That the expected product was obtained was confirmed by the spectral data: M.S. (E.I.): 315 (M+); NMR (CDCl3): δ8.0 (1H, d), 7.6 (1H, dd), 7.35 (1H, dd), 7.2 (1H, dd), 4.25 (2H, m, CH2N), 3.98 (3H, s, OCH3), 2.65 (3H, s, C(O)CH3), 1.8 (2H, m), 1.35 (8H, m), 0.9 (3H, t, CH3).

Provenance & Evidence