Methyl iodide → 7-Bromo-8-methoxyquinoline

HRID 1525916Notes

Reaction equation

HRID 1525916 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:16]>CN(C)C=O>[Br:1][C:2]1[C:11]([O:12][CH3:16])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3841617-Bromo-8-hydroxyquinoline

Product 1

HCID 111181027-Bromo-8-methoxyquinolineYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an oven dried round bottom flask under nitrogen, a solution of 7-bromoquinolin-8-ol (1 g, 4.46 mmol) in N,N-dimethylformamide (20 mL) at room temperature was treated with sodium hydride (60% dispersion in mineral oil, 0.268 g, 6.69 mmol) to give a bright yellow mixture and was stirred for 3 min. Iodomethane (0.307 mL, 4.91 mmol) was then added by syringe and the reaction was stirred for 30 min. The reaction was quenched carefully with water (50 mL) and diluted with ethyl acetate (100 mL). The layers were separated and the organic layer was dried over magnesium sulfate and concentrated in vacuo to give a liquid, which solidified to a white solid (1.06 g, quantitative yield) on standing overnight. MS(ES)+ m/e 237.8, 239.7 [M+H]+.

Workup

  1. customIn an oven dried round bottom flask under nitrogen
  2. customto give a bright yellow mixture
  3. stirringthe reaction was stirred for 30 min
  4. customThe reaction was quenched carefully with water (50 mL)
  5. additiondiluted with ethyl acetate (100 mL)
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a liquid, which

Sources & evidence

ORD record
ord-b122ef4ee89d4bbb8c4a27a1db87cb25
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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