6-Hydroxyquinoline → HCID 18442909, compound

HRID 458724Notes

Reaction equation

HRID 458724 reaction equation
[OH-].[K+].[N:3]1[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Br[CH2:15][CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1>C(O)C>[N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:15][CH2:16][O:17][C:18]3[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 113746-HydroxyquinolineHCID 14797Potassium HydroxideHCID 2627064-(2-Bromoethoxy)Benzaldehyde

Product 1

HCID 18442909HCID 18442909, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of potassium hydroxide (0.67 g, 9.80 mmol) in ethanol (30 ml) is added 6-quinolinol (1.42 g, 9.80 mmol) and 4-(2-bromoethoxy)benzaldehyde (2.25 g, 9.80 mmol). Then the mixture is heated to reflux for 8 hours. After cooled to −5° C., the precipitate is collected by filtration, washed with water, and dried under vacuum to give the title product (1.26 g, 44%).

Workup

  1. temperatureThen the mixture is heated
  2. temperatureto reflux for 8 hours
  3. filtrationthe precipitate is collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-46108153def34390919b999e539e5e54
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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