Trifluoroacetic acid → (7-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]=[C:14]([CH3:17])[CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:18].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH3:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][C:8](=[O:18])[N:7]2[CH2:6][CH:2]=[O:1])=[CH:12][CH:13]=1Participants
Procedure
To 0.37 g of 1-(1,3-dioxolan-2-ylmethyl)-7-methylquinolin-2(1H)-one, 3.7 mL of a 90% aqueous trifluoroacetic acid solution was added, the mixture was stirred at room temperature for 1 hour, and the solvent was removed under reduced pressure. The residue thus obtained was added with ethyl acetate and an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and an 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 0.32 g of a brown oily substance, (7-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde.
Workup
- customthe solvent was removed under reduced pressure
- customThe residue thus obtained
- customThe organic layer was separated
- extractionthe aqueous layer was extracted twice 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-c24ca3de77ec4b42bf14538ad94d2a88
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329694B2
Reaction notes
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