Diethyl Ether → 8-Acetylquinoline

HRID 2113124Notes

Reaction equation

HRID 2113124 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2)=[O:5].[CH3:17][Mg]I.C(OCC)C>C1COCC1.C(=O)=O>[N:14]1[C:15]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[C:4](=[O:5])[CH3:17])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 20803291N-methoxy-N-methylquinoline-8-carboxamideHCID 178418373HCID 178418373, compound

Product 1

HCID 122087898-AcetylquinolineYield 83%

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Quinoline-8-carboxylic acid methoxy-methyl-amide (2.16 g, 10 mmol) was dissolved in anhydrous THF (40 mL) and cooled to −78° C. The 3 M methyl magnesium iodide solution in diethyl ether (4.0 mL, 12 mmol, Aldrich) was slowly added to the reaction solution in dry ice bath. The reaction mixture was allowed to stir under nitrogen at room temperature for overnight then the reaction was cooled at ice bath and quenched with saturated aqueous ammonium chloride (40 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (30 mL×2). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated via vacuo to give crude title compound as light yellow solid in 83% yield (1.42 g, 8.3 mmol).

Workup

  1. temperaturethe reaction was cooled at ice bath
  2. customquenched with saturated aqueous ammonium chloride (40 mL)
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (30 mL×2)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated via vacuo

Sources & evidence

ORD record
ord-df7199d945ca4d17a93fcc0b7fe1179c
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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