Potassium Iodide → Acetonitrile, [(5,7-dichloro-2-methyl-8-quinolinyl)oxy]-

HRID 2231942Notes

Reaction equation

HRID 2231942 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:24][C:25]#[N:26]>CC(=O)CC.O>[CH3:14][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[C:9]([O:13][CH2:24][C:25]#[N:26])[C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[N:7]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 63015,7-Dichloro-8-hydroxy-2-methylquinolineHCID 7856ChloroacetonitrileHCID 11430Potassium Carbonate

Product 1

HCID 2681672Acetonitrile, [(5,7-dichloro-2-methyl-8-quinolinyl)oxy]-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

10.7 g of 5,7-dichloro-8-hydroxyquinaldine are dissolved at elevated temperature in 150 ml of 2-butanone; 10.4 g of potassium carbonate are then added portionwise, and the mixture is refluxed for one hour. After the addition of 1 g of potassium iodide, there are added dropwise, with stirring and refluxing, 7.1 g of chloroacetonitrile in 30 ml of 2-butanone, and the mixture is subsequently heated for 3 hours at an internal temperature of 75° C. To the resulting reaction mixture, after cooling to room temperature, is added 1 liter of water, and the whole is filtered; the residue is washed with water, dried, and recrystallised from chloroform/petroleum ether (40°-60° C.) to thus obtain 2-methyl-5,7-dichloro-8-(cyanomethoxy)-quinoline, m.p. 157°-158° C.

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. additionare added dropwise
  3. temperaturerefluxing
  4. customTo the resulting reaction mixture
  5. filtrationthe whole is filtered
  6. washthe residue is washed with water
  7. customdried
  8. customrecrystallised from chloroform/petroleum ether (40°-60° C.) to thus obtain 2-methyl-5,7-dichloro-8-(cyanomethoxy)-quinoline, m.p. 157°-158° C.

Sources & evidence

ORD record
ord-afe7ef70eec1406c8cdb4ec6330d0aa0
Source dataset
uspto-grants-1988_11
Patent number
US04785105

Reaction notes

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