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

HRID 36056Notes

Reaction equation

HRID 36056 reaction equation
[CH3:1][Li].[CH2:3]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([O:20][CH3:21])=[C:12]([C:22]([O:24]CC)=O)[C:11]1=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>C1COCC1.[Cu]I>[CH2:3]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([O:20][CH3:21])=[C:12]([C:22](=[O:24])[CH3:1])[C:11]1=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 212178031-Heptyl-3-Ethoxycarbonyl-4-Methoxy-2(1H)-QuinolinoneHCID 178418348HCID 178418348, compound

Product 1

HCID 212178081-Heptyl-3-Acetyl-4-Methoxy-2(1H)-QuinolinoneYield 75%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  1. customthe reaction was quenched with saturated ammonium chloride
  2. customThe product was isolated by acidification of the reaction to pH 5, and extraction (3×) with ethyl acetate
  3. customFinal purification on Silica-Gel 60 (4:1 hexane:ethyl acetate eluent)

Sources & evidence

ORD record
ord-a2985cc768474f0a97002ce55d7a60c2
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Reaction notes

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