Pyridine → 3-Bromoquinolin-6-yl acetate

HRID 1890933Notes

Reaction equation

HRID 1890933 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Br:21]Br>C(Cl)(Cl)(Cl)Cl>[Br:21][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][C:7]([O:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 459602quinolin-6-yl acetate

Product 1

HCID 685300473-Bromoquinolin-6-yl acetateYield 63.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of acetic acid quinolin-6-yl ester (120 g, 0.642 mol) and pyridine (114 mL, 1.41 mol) in 6 L of CCl4 was added Br2 (66 mL, 1.28 mol) dropwise. The mixture was heated to reflux for 2 hours before being 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 partitioned between aqueous NaHCO3 and dichloromethane. The combined organic layers were washed with water again and dried before being evaporated to dryness in vacuo. The crude product was purified through flash column chromatography eluting with Petroleum Ether/ethyl acetate (10/1˜1/1) to provide 108 g of acetic acid 3-bromo-quinolin-6-yl ester as a yellow solid (63% yield).

Workup

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

Sources & evidence

ORD record
ord-e8ac561047024808b09947852f769075
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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