Methyl iodide → 2-Ethyl-8-methoxyquinoline

HRID 2393082Notes

Reaction equation

HRID 2393082 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=C(C)C=[CH:13]2.IC>O1CCCC1>[CH2:3]([C:2]1[CH:1]=[CH:13][C:12]2[C:17](=[C:8]([O:7][CH3:6])[CH:9]=[CH:10][CH:11]=2)[N:16]=1)[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 3169868-Methoxy-2-MethylquinolineHCID 178418339Butyllithium

Product 1

HCID 154560072-Ethyl-8-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

n-Butyllithium (1 ml, 1.6M in hexanes) was added dropwise to a stirred solution of 8-methoxy-2-methylquinoline (0.25 g) in tetrahydrofuran (4 ml) at -60° C. under an inert atmosphere. The resulting red solution was stirred at -60° C. for 15 minutes, and then warmed to -40° C. Iodomethane (0.27 ml) was then added dropwise and the reaction warmed slowly to room temperature with continued stirring for 12 hours. The reaction was quenched with brine (50 ml) and extracted with dichloromethane (2×5ml). The organic phases were combined, dried over magnesium sulphate and preadsorbed onto silica. Purification was achieved by column chromatography eluting with ethyl acetate to afford the title compound as a pale yellow solid (0.16 g).

Workup

  1. temperaturewarmed to -40° C
  2. temperaturethe reaction warmed slowly to room temperature
  3. stirringwith continued stirring for 12 hours
  4. customThe reaction was quenched with brine (50 ml)
  5. extractionextracted with dichloromethane (2×5ml)
  6. dry with materialdried over magnesium sulphate
  7. customPurification
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-81b6a862622a4915ae8f28d4ced07fb5
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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