Sodium ethoxide → 6-Bromo-4-ethoxyquinoline

HRID 852989Notes

Reaction equation

HRID 852989 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.[O-:13][CH2:14][CH3:15].[Na+]>C(O)C.C(=O)(O)[O-].[Na+]>[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:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 586153986-Bromo-4-ethoxyquinolineYield 90.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 6-bromo-4-chloroquinoline (17 g, 70.10 mmol) in ethanol (400 mL) was added sodium ethoxide (23.85 g, 350.5 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 ethanol was removed under the vacuum and the residue was diluted with water. The aqueous suspension was neutralized with 3.0N hydrochloric acid until the precipitate formed and later it was diluted with saturated sodium bicarbonate solution. Then, the solids were collected by filtration and washed with water. After drying in air, 15.94 g (90.2% yield) of 6-bromo-4-ethoxy-quinoline was isolated as a white solid which can be crystallized from acetonitrile: EI-HRMS m/e calcd for C11H10BrNO (M+) 250.9946, found 250.9946.

Workup

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

Sources & evidence

ORD record
ord-5b83827849b44cdf8ee3784a67aae9a0
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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