Methanol → HCID 22320369, compound

HRID 498017Notes

Reaction equation

HRID 498017 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:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12.[CH3:22][O-:23].[Na+].CO>O1CCCC1>[CH3:22][O:23][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:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12

Participants

5

Reactant 3

HCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 22320369HCID 22320369, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.00 g, 3.39 mmol) and 28% sodium methoxide in methanol (9.69 g, 50.2 mmol) were added to a mixture of methanol (30 mL) and tetrahydrofuran (30 mL), and the solution was heated under reflux for 2.5 hours. After the solution was cooled to room temperature, the solvents were evaporated under reduced pressure. The residue was poured into water, and the organic matter was extracted with ethyl acetate. The extract was washed with saturated brine 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 (hexane:ethyl acetate=1:1 to ethyl acetate) to give the title compound (0.73 g, 50% yield).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 2.5 hours
  3. customthe solvents were evaporated under reduced pressure
  4. additionThe residue was poured into water
  5. extractionthe organic matter was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-fa5d81f328d24904943e50b76c9291f7
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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