Sodium Methoxide → 7-Bromo-2-methoxy-4-methylquinoline

HRID 280000Notes

Reaction equation

HRID 280000 reaction equation
Cl[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([Br:13])=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][O-:15].[Na+]>CO>[CH3:14][O:15][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([Br:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 145703037-Bromo-2-chloro-4-methylquinoline

Product 1

HCID 145703057-Bromo-2-methoxy-4-methylquinolineYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.00 g (12.00 mM) of 2-chloro-4-methyl-7-bromoquinoline and 0.63 g (12.00 mM) of sodium methoxide was heated to reflux in 30 mL of dry methanol for 48 h. The methanol was then removed in vacuo, and the resultant concentrate was taken up in methylene chloride. This methylene chloride solution was washed repeatedly with saturated sodium chloride. After drying (MgSO4), solvent removal, and recrystallisation from toluene, 2.63 g (87%) of the product was obtained as white crystals: mp 58°-60° C.

Workup

  1. temperaturewas heated
  2. customThe methanol was then removed in vacuo
  3. concentrationthe resultant concentrate
  4. washThis methylene chloride solution was washed repeatedly with saturated sodium chloride
  5. customAfter drying
  6. custom(MgSO4), solvent removal, and recrystallisation from toluene

Sources & evidence

ORD record
ord-472bb6864b6445498dd82e522fb16917
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Reaction notes

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