8-Hydroxyquinoline → HCID 66918112, compound

HRID 1818000Notes

Reaction equation

HRID 1818000 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[OH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 703202-Bromomethylnaphthalene

Product 1

HCID 66918112HCID 66918112, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(bromomethyl) naphthalene (663 mg, 3 mmol) was added to a stirred mixture of 8-hydroxy quinoline (435 mg, 3 mmol), K2CO3 (621 mg, 4.5 mmol) in acetone (20 ml) at room temperature. The reaction mixture was stirred at rt over weekend and then partitioned between EtOAc and water. Water layer was extracted with EtOAc (2×100 ml). The combined organic phase was washed with water (2×100 ml), brine and dried over sodium sulfate. After removal of solvent, the residue was washed with ether to give 650 mg of compound I-81. 1H-NMR (500 MHz, CDCl3).

Workup

  1. custompartitioned between EtOAc and water
  2. extractionWater layer was extracted with EtOAc (2×100 ml)
  3. washThe combined organic phase was washed with water (2×100 ml), brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of solvent
  6. washthe residue was washed with ether

Sources & evidence

ORD record
ord-712437a9b9704f45ba422305726b4bee
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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