5-Chloro-8-hydroxyquinoline → HCID 18968588, compound

HRID 398737Notes

Reaction equation

HRID 398737 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

7

Reactant 4

HCID 28175-Chloro-8-hydroxyquinolineHCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 18968588HCID 18968588, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

10.0 mmol of 5-chloro-8-hydroxyquinoline (ALDRICH) are dissolved, with stirring, in 20 ml of dry DMF, in a 50 ml round-bottomed flask provided with stirring and a thermometer. Then 11 mmol of potassium carbonate and 10% by weight of potassium iodide are added. A solution of 11 mmol of benzyl chloride (JANSSEN) in 5 ml of DMF is added dropwise over 5 minutes, at room temperature and with stirring. After 18 hours of reaction at 50° C., the reaction mixture, supplemented with 100 ml of water is extracted with 4×50 ml of tert-butyl methyl ether. The organic phases are combined, then washed with 3×50 ml of 1N HCl. The aqueous phases are combined, alkalized to pH=9 and extracted with 2×50 ml of ethyl acetate. After drying the organic phase over MgSO4, the solvent is evaporated under reduced pressure. The desired product is obtained after recrystallization from ethanol.

Workup

  1. customprovided
  2. stirringwith stirring
  3. customAfter 18 hours of reaction at 50° C.
  4. extractionis extracted with 4×50 ml of tert-butyl methyl ether
  5. washwashed with 3×50 ml of 1N HCl
  6. extractionextracted with 2×50 ml of ethyl acetate
  7. dry with materialAfter drying the organic phase over MgSO4
  8. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-86ed1119e78f4695b5819a23d41fa2a0
Source dataset
uspto-grants-1998_10
Patent number
US05817520

Reaction notes

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