Hydrochloric Acid → 3-Methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one
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.Cl.C([OH:25])C>>[CH3:15][C:14]1[C:3]2[C:2](=[O:25])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[N:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:13]=1Participants
4
Procedure
To a solution of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (34.9 g, 0.12 mol) in ethanol (500 mL) was added 6N hydrochloric acid (50 mL, 0.30 mol), and the mixture was heated under reflux for 2 hours. The solution was cooled to room temperature, and concentrated under reduced pressure. The residue was made basic by the addition of an aqueous sodium hydroxide solution, and the organic matter was extracted with chloroform. 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 was purified by silica gel column chromatography (chloroform:methanol=95:5) to give the title compound (25.8 g, 79% yield).
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 2 hours
- concentrationconcentrated under reduced pressure
- additionThe residue was made basic by the addition of an aqueous sodium hydroxide solution
- extractionthe organic matter was extracted with chloroform
- washThe extract was washed with saturated brine and water
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (chloroform:methanol=95:5)
Sources & evidence
- ORD record
- ord-5a3f074bce2c4d7c9b4355ce77ce94a9
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06949648B2
Reaction notes
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