1-Butanol → HCID 22320271, compound

HRID 498019Notes

Reaction equation

HRID 498019 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), sodium hydride (oiliness, content 60%, 0.41 g, 17 mmol) was added at room temperature and the mixture was stirred for 15 minutes. Subsequently, 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.0 g, 3.39 mmol) was added to the mixture at 0° C., and the mixture was heated under reflux for another 1 hour. After the reaction solution was cooled to room temperature, the reaction solvent was concentrated and evaporated under reduced pressure. To the reaction mixture was added iced water and the mixture was neutralized by the addition of dilute hydrochloric acid, and the organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and water and 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. temperaturethe mixture was heated
  2. temperatureunder reflux for another 1 hour
  3. concentrationthe reaction solvent was concentrated
  4. customevaporated under reduced pressure
  5. additionTo the reaction mixture was added iced water
  6. additionthe mixture was neutralized by the addition of dilute hydrochloric acid
  7. extractionthe organic matter was 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-e97b3b9a6498491ba2d3d0cd2203bd7a
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

Loading…