Sodium Chloride → HCID 43668467, compound

HRID 1966531Notes

Reaction equation

HRID 1966531 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[H-].[Na+].[CH2:16](I)[CH2:17][CH3:18].[Na+].[Cl-]>CN(C)C=O>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH2:16][CH2:17][CH3:18])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 43668467HCID 43668467, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Chloro-8-hydroxy-2-methylquinoline (500 mg, 2.58 mmole) was suspended in dimethylformamide (4 mL) and mixed with sodium hydride (60% in paraffin liq., 113 mg). After stirring for 1 h, propyliodide (461 mg, 2.71 mmole) in dimethylformamide (1 mL) was added dropwise and the mixture was kept under stirring at RT for 16 hrs. Diluted NaCl solution was added and the mixture was extracted with ethyl acetate. The organic phases were dried, concentrated and the residue thus obtained was purified using silica gel chromatography, eluting with dichloromethane:methanol 95:5. Precipitation in isopropanol/iso-propyl ether/HCl gave the product (300 mg, 49%).

Workup

  1. stirringunder stirring at RT for 16 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic phases were dried
  4. concentrationconcentrated
  5. customthe residue thus obtained
  6. customwas purified
  7. washeluting with dichloromethane:methanol 95:5
  8. customPrecipitation in isopropanol/iso-propyl ether/HCl

Sources & evidence

ORD record
ord-f0b7889f7a8a4b96bfd5499621f3761f
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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