Sodium Methoxide → 5-Bromo-2-methoxyquinoline

HRID 2090046Notes

Reaction equation

HRID 2090046 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](Cl)=[N:7]2.[CH3:13][O-:14].[Na+]>CO.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:14][CH3:13])=[N:7]2

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 142210335-Bromo-2-chloroquinoline

Product 1

HCID 142209695-Bromo-2-methoxyquinoline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 5-bromo-2-chloroquinoline (2.81 g, 11.6 mmol) in MeOH (25 mL) was added sodium methoxide (30% w/w in MeOH, 10.4 mL, 54.7 mmol). The mixture was refluxed for 3 hours, allowed to cool to room temperature, diluted with water, then extracted with EtOAc. The combined extracts were washed with water then saturated NaCl (aq), dried over Na2SO4, filtered, then concentrated to afford the title compound as a white solid: 1H NMR (500 MHz, CDCl3): δ 8.36 (d, J=9.1 Hz, 1H); 7.81 (d, J=8.4 Hz, 1H); 7.63 (dd, J=7.6, 1.1 Hz, 1H); 7.46 (t, 1H, J=7.9 Hz); 6.98 (d, J=9.1 Hz, 1H); 4.08 (s, 3H); LC1 1.85 min. (M+H) 238.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with water
  4. dry with materialsaturated NaCl (aq), dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a89b73a22c1045fe82475c6c6fd5084e
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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