Trifluoroacetic acid → (7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde
Reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[N: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])=[N:12][CH:13]=1Participants
Conditions
- Temperature
- 65 °C
Procedure
To 0.11 g of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one, 6.0 mL of an 80% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at 60 to 70° C. for 1 hour. Thereto was added 4.0 mL of an 80% aqueous trifluoroacetic acid solution, and the mixture was stirred at 60 to 70° C. for 1 hour. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The resultant residue was charged with ethyl acetate and water and adjusted to pH 7.0 with a 1 mol/L aqueous sodium hydroxide solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined and the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.11 g of (7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde as a light brown foam.
Workup
- stirringthe mixture was stirred at 60 to 70° C. for 1 hour
- temperatureThe reaction mixture was cooled to room temperature
- distillationthe solvent was distilled off under reduced pressure
- additionThe resultant residue was charged with ethyl acetate and water
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-1c726d698e5745629b4ba4c1fe6d355b
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367831B2
Reaction notes
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