1-Butanol → HCID 22320271, compound

HRID 497967Notes

Reaction equation

HRID 497967 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]2[N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:20]=[C:21]([CH3:22])[C:10]=12>O1CCCC1>[CH2:1]([O:5][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]2[N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:20]=[C:21]([CH3:22])[C:10]=12)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 24758Sodium hydrideHCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 22320271HCID 22320271, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of 1-butanol (5.0 g, 68 mmol) in tetrahydrofuran (15 mL) was added sodium hydride (oiliness, content 60%, 0.41 g, 17 mmol), and the mixture was stirred at room temperature for 15 minutes. After 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.0 g, 3.39 mmol) was added thereto at 0° C., the mixture was heated under reflux further for 1 hour. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated and concentrated under reduced pressure. Iced water was added to the residue and the mixture was neutralized with dilute hydrochloric acid, and organic matter was extracted with ethyl acetate. 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 (ethyl acetate) to give the title compound (0.29 g, 26% yield).

Workup

  1. temperatureat 0° C., the mixture was heated
  2. temperatureunder reflux further for 1 hour
  3. temperatureto cool to room temperature
  4. customthe solvent was evaporated
  5. concentrationconcentrated under reduced pressure
  6. additionIced water was added to the residue
  7. extractionwas extracted with ethyl acetate
  8. washThe extract was washed with saturated brine and water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-fd31ca305a5d4048b82b969d75455d51
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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