Methyl iodide → 8-Methoxy-2-Methylquinoline

HRID 2393080Notes

Reaction equation

HRID 2393080 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[OH-].[Na+].[CH3:15]I>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>[CH3:15][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 132242-Methyl-8-hydroxyquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 3169868-Methoxy-2-Methylquinoline

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-hydroxyquinaldine (5.0 g) and tetrabutyl ammonium iodide (1.1 g) in tetrahydrofuran (9 ml) was treated at room temperature with sodium hydroxide (4.5 g) in water (45 ml). Methyl iodide (3.7 ml) was added and the reaction stirred overnight. The THF was removed in vacuo and the remaining solution partitioned between ethyl acetate (100 ml) and water (100 ml). The aqueous layer was re-extracted with ethyl acetate and the organic extracts combined. The organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and saturated aqueous sodium chloride (100 ml). The organic layer was dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo to yield the desired product as an off-white solid (5.85 g).

Workup

  1. customThe THF was removed in vacuo
  2. customthe remaining solution partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. extractionThe aqueous layer was re-extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and saturated aqueous sodium chloride (100 ml)
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-9c20a7f70511409193857640867f48e8
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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