Pyridine → 5-Bromo-6-methoxyquinoline

HRID 1890928Notes

Reaction equation

HRID 1890928 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.N1C=CC=CC=1.[Br:19]Br>C(Cl)(Cl)(Cl)Cl>[Br:19][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 148606-MethoxyquinolineHCID 24408Bromine

Product 1

HCID 184141285-Bromo-6-methoxyquinolineYield 36%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 6-methoxy-quinoline (13.0 g, 0.082 mol) and pyridine (13.2 mL, 0.164 mol) in CCl4 (130 mL) was added bromine (8.4 mL, 0.164 mol) dropwise. The mixture was heated to reflux for 2 hrs and cooled to room temperature. The liquid in the flask was decanted and washed with saturated aqueous NaHCO3 and water. The dark solid on the bottom of the flask was treated with NaHCO3 and dichloromethane. The combined organic layers were washed with water again and dried before being evaporated to dryness. The crude product was purified by flash column chromatography eluting with petroleum ether/ethyl acetate (10/1˜1/1) to give 7 g of 5-bromo-6-methoxy-quinoline as a red solid (36% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hrs
  3. customThe liquid in the flask was decanted
  4. washwashed with saturated aqueous NaHCO3 and water
  5. additionThe dark solid on the bottom of the flask was treated with NaHCO3 and dichloromethane
  6. washThe combined organic layers were washed with water again
  7. customdried
  8. custombefore being evaporated to dryness
  9. customThe crude product was purified by flash column chromatography
  10. washeluting with petroleum ether/ethyl acetate (10/1˜1/1)

Sources & evidence

ORD record
ord-1cc6062be52149388961153c54dd3bb9
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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