Sodium Hydroxide → HCID 67041249, compound

HRID 606138Notes

Reaction equation

HRID 606138 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[C:8]1([C:14]2[O:18][N:17]=[C:16]([CH2:19][NH:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=[CH:23][C:22]=3[NH2:31])[CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>C(#N)C>[CH2:1]([O:3][CH2:4][C:5]1[N:20]([CH2:19][C:16]2[CH:15]=[C:14]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[O:18][N:17]=2)[C:21]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[CH:23][C:22]=2[N:31]=1)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 84189Ethoxyacetyl chlorideHCID 86247653HCID 86247653, compound

Product 1

HCID 67041249HCID 67041249, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of ethoxyacetyl chloride (0.87 g, 7.1 mmol) in acetonitrile (10 mL) was added to a solution of N4-[(5-phenylisoxazol-3-yl)methyl]quinoline-3,4-diamine (2.05 g, 6.48 mmol) in acetonitrile (100 mL), and the solution was stirred at room temperature overnight. The volatiles were removed under reduced pressure, and the residue was dissolved in 3:1 ethanol:water (100 mL). Solid sodium hydroxide (389 mg, 9.72 mmol) was added, and the solution was heated at reflux overnight. The ethanol was removed under reduced pressure, and the resultant aqueous solution was adjusted to pH 5 with the additional of dilute hydrochloric acid. The acidic solution was extracted several times with dichloromethane, and the combined organic fractions were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (eluting with 4% to 6% methanol in dichloromethane to provide 0.650 g of 2-(ethoxymethyl)-1-[(5-phenylisoxazol-3-yl)methyl]-1H-imidazo[4,5-c]quinoline as a white solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in 3:1 ethanol
  3. temperaturethe solution was heated
  4. temperatureat reflux overnight
  5. customThe ethanol was removed under reduced pressure
  6. extractionThe acidic solution was extracted several times with dichloromethane
  7. washthe combined organic fractions were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by flash column chromatography on silica gel (
  12. washeluting with 4% to 6% methanol in dichloromethane

Sources & evidence

ORD record
ord-151a9e0969ca4150b41ad127406db05c
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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