6-Bromo-4-chloroquinoline → 6-Bromo-4-methoxyquinoline

HRID 852985Notes

Reaction equation

HRID 852985 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[CH3:13][O-:14].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[O:14][CH3:13]

Participants

4

Reactant 2

HCID 51395376-Bromo-4-chloroquinolineHCID 10942334Sodium Methoxide

Product 1

HCID 457909296-Bromo-4-methoxyquinolineYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 6-bromo-4-chloro-quinoline (12.12 g, 50 mmol) in methanol (200 mL) was added sodium methoxide (13.50 g, 250 mmol) at room temperature. Then, the reaction mixture was heated to 120° C. for 15 h in a sealed reaction flask. After cooling to room temperature, the methanol was removed under the vacuum and the residue was diluted with water. Then, the solids were collected by filtration and washed with water. After drying in air, 10.8 g (90.8% yield) of 6-bromo-4-methoxy-quinoline was isolated as a white solid which can be crystallized from acetonitrile: EI-HRMS m/e calcd for C10H8BrNO (M+) 236.9789, found 236.9784.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe methanol was removed under the vacuum
  3. additionthe residue was diluted with water
  4. filtrationThen, the solids were collected by filtration
  5. washwashed with water
  6. customAfter drying in air

Sources & evidence

ORD record
ord-61b3efb569674f40803d27245218fd78
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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