Pyridine → 7-Methyl-2-propylthiazolo[4,5-c]quinoline
Reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].O[C:16]1(NC(=O)CCC)[C:25]2[C:20](=[CH:21][C:22]([CH3:26])=[CH:23][CH:24]=2)[N:19]=[CH:18][CH2:17]1.[N:33]1C=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH3:26][C:22]1[CH:23]=[CH:24][C:25]2[C:16]3[S:2][C:34]([CH2:35][CH2:36][CH3:37])=[N:33][C:17]=3[CH:18]=[N:19][C:20]=2[CH:21]=1Participants
Procedure
Under a nitrogen atmosphere, phosphorus pentasulfide (1.15 g, 2.6 mmol) was added to a mixture of N-(4-hydroxy-7-methylquinolin-4-yl)butyramide (630 mg, 2.6 mmol) in pyridine (20 mL). The reaction mixture was heated to reflux. The reaction mixture turned bright yellow and all of the solid went into solution. The reaction mixture was heated at reflux for about 2 hours and then allowed to cool to ambient temperature. The reaction mixture was extracted with water, aqueous sodium bicarbonate and dichloromethane. The organic layer was treated with saturated copper sulfate, dried with magnesium sulfate and then concentrated under vacuum to provide an oil. The oil was dried under high vacuum to provide 410 mg of 7-methyl-2-propylthiazolo[4,5-c]quinoline as an orange solid.
Workup
- temperatureThe reaction mixture was heated to reflux
- temperatureThe reaction mixture was heated
- temperatureat reflux for about 2 hours
- extractionThe reaction mixture was extracted with water, aqueous sodium bicarbonate and dichloromethane
- additionThe organic layer was treated with saturated copper sulfate
- dry with materialdried with magnesium sulfate
- concentrationconcentrated under vacuum
- customto provide an oil
- customThe oil was dried under high vacuum
Sources & evidence
- ORD record
- ord-e9cce14f2ae04a1b828a6322e5c23c84
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06440992B1
Reaction notes
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