Trifluoroacetic acid → (8-methyl-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]=[CH:14][C:15]=2[CH3:17])[CH:10]=[CH:9][C:8]1=[O:18].FC(F)(F)C(O)=O>>[CH3:17][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[N:7]([CH2:6][CH:2]=[O:1])[C:8](=[O:18])[CH:9]=[CH:10]2Participants
Conditions
- Temperature
- 40 °C
Procedure
To 0.17 g of 1-(1,3-dioxolan-2-ylmethyl)-8-methylquinolin-2(1H)-one, 2 mL of a 90% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at room temperature for 4 days, at 40° C. for 3 days, and at room temperature for 5 days. The solvent was removed under reduced pressure, and the reaction mixture was added with ethyl acetate and an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.14 g of a brown oily substance, (8-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde.
Workup
- waitat room temperature for 5 days
- customThe solvent was removed under reduced pressure
- additionthe reaction mixture was added with ethyl acetate
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washthe resultant solution was washed with an aqueous saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-107b4fe204144bcb9cc1d7668ea6b5b5
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524738B2
Reaction notes
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