Trifluoroacetic acid → (7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde
Reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:19].FC(F)(F)C(O)=O>>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][C:8](=[O:19])[N:7]2[CH2:6][CH:2]=[O:1])=[CH:12][CH:13]=1Participants
Procedure
To 0.56 g of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxyquinolin-2(1H)-one, 5.6 mL of a 90% aqueous trifluoroacetic acid solution was added, the mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, water and chloroform was added thereto, and the reaction mixture was adjusted to pH 7.0 with an aqueous saturated sodium hydrogen carbonate solution and stirred for 2 hours. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.36 g of a yellow oily substance, (7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde.
Workup
- customThe solvent was removed under reduced pressure, water and chloroform
- additionwas added
- stirringstirred for 2 hours
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with chloroform
- washthe resultant solution was washed sequentially with water
- dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-e34977aafc8548a997be1ebe04cd5406
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329694B2
Reaction notes
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