Ethanol → HCID 135848085, compound

HRID 498068Notes

Reaction equation

HRID 498068 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:13]=[CH:14][C:3]=12.C([OH:23])C>Cl>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:12]1[C:4]2[NH:5][C:6]3[C:11]([C:2](=[O:23])[C:3]=2[CH:14]=[N:13]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 2

HCID 702EthanolHCID 22320298HCID 22320298, compound

Product 1

HCID 135848085HCID 135848085, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 4-chloro-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (14 g, 0.050 mol) in ethanol (600 mL), 6N hydrochloric acid (30 mL) was added and the mixture was heated under reflux for 12 hours. The reaction solution was allowed to cool to room temperature, and concentrated and evaporated under reduced pressure. The residue was made basic by addition of an aqueous sodium hydroxide solution, and the organic matter was extracted with chloroform. The extract was washed with saturated brine and water, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform:methanol=96:4) to give the title compound (10.8 g, 82% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. concentrationconcentrated
  4. customevaporated under reduced pressure
  5. additionThe residue was made basic by addition of an aqueous sodium hydroxide solution
  6. extractionthe organic matter was extracted with chloroform
  7. washThe extract was washed with saturated brine and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography (chloroform:methanol=96:4)

Sources & evidence

ORD record
ord-2aa409e31a81442e87ab26dc7d915a4e
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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