Water → HCID 19075044, compound

HRID 964996Notes

Reaction equation

HRID 964996 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([Br:13])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH3:21].O>CN(C)C=O.C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:20][CH3:21])=[CH:9][CH:10]=2)[N:5]=[C:4]([Br:13])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 135829331HCID 135829331, compound

Product 1

HCID 19075044HCID 19075044, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-Chloro(bromo)-7-hydroxyquinoline (200 mg) dissolved in N,N-dimethylformamide (DMF; 30 ml) was added with potassium carbonate (203 mg) and ethyl iodide (232 mg) and stirred at room temperature for 8 hours. The reaction mixture was added with water (50 ml) and methylene chloride (30 ml) and shaken to separate the organic layer. Further, the water layer was extracted three times with methylene chloride (30 ml). This extract solution was combined with the above-mentioned organic layer, washed with saturated saline solution and dried over magnesium sulfate. This extract solution was detected by thin-layer chromatography (TLC; MERCK, Art. 5554, methylene chloride : methanol=9 : 1) to find UV (254 nm) absorptive spots at Rf values of 0.7 and 0.4. After drying, the solvent was removed under reduced pressure from the extract solution. The residue was chromatographed by silica gel column chromatography (Wako Gel™ C-200, methylene chloride : methanol=9 : 1). Fractions corresponding to Rf value of 0.7 were collected and evaporated to obtain the aimed 4-chloro(bromo)-7-ethoxy-quinoline (185 mg). MS m/z: 207 (M+, 4-Cl derivative) and 251(M+, 4-Br derivative)

Workup

  1. stirringshaken
  2. customto separate the organic layer
  3. extractionFurther, the water layer was extracted three times with methylene chloride (30 ml)
  4. washwashed with saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. customAfter drying
  7. customthe solvent was removed under reduced pressure from the extract solution
  8. customThe residue was chromatographed by silica gel column chromatography (Wako Gel™ C-200, methylene chloride : methanol=9 : 1)
  9. customFractions corresponding to Rf value of 0.7 were collected
  10. customevaporated

Sources & evidence

ORD record
ord-9578c6be1d514aca854c45a070da6c3f
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

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