Methyl iodide → 7-Methoxyquinoline

HRID 1520177Notes

Reaction equation

HRID 1520177 reaction equation
[H-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[CH3:14]I>CN(C)C=O>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7]([CH:6]=[CH:5][CH:4]=[N:3]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1354268667-Hydroxyquinoline

Product 1

HCID 786667-MethoxyquinolineYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of sodium hydride (5.5 g, 137.50 mmol, 60%) in N,N-dimethylformamide (150 ml) was added quinolin-7-ol (8 g, 55.11 mmol). The reaction was stirred for 1 h at 0° C. in a water/ice bath. Then CH3I (7.84 g, 55.23 mmol) was added and the solution was stirred for an additional 1 h at room temperature. The reaction was then quenched by the addition of water/ice (700 ml) and extracted with ethyl acetate (3×200 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo to give a residue, which was purified by a silica gel column with 6% ethyl acetate in petroleum ether to afford 7-methoxyquinoline as a red oil (5.5 g, 63%).

Workup

  1. stirringthe solution was stirred for an additional 1 h at room temperature
  2. customThe reaction was then quenched by the addition of water/ice (700 ml)
  3. extractionextracted with ethyl acetate (3×200 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a residue, which
  7. customwas purified by a silica gel column with 6% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-e77ac40b53194bb9bb03ac77cddd9877
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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