Trifluoroacetic acid → (2-oxoquinolin-1(2H)-yl)acetaldehyde

HRID 2193062Notes

Reaction equation

HRID 2193062 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:17].FC(F)(F)C(O)=O>>[O:17]=[C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]1[CH2:6][CH:2]=[O:1]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593978641-(1,3-dioxolan-2-ylmethyl)quinolin-2(1H)-one

Product 1

HCID 17781681(2-oxoquinolin-1(2H)-yl)acetaldehydeYield 77.2%

Procedure

To 0.88 g of 1-(1,3-dioxolan-2-ylmethyl)quinolin-2(1H)-one, 8.8 mL of a 90% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, thereto were added an aqueous saturated sodium hydrogen carbonate solution and ethyl acetate, and the mixture was stirred at room temperature for 30 minutes. The organic layer was separated, and the aqueous layer was extracted 5 times with ethyl acetate. The organic layer and an extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.55 g of (2-oxoquinolin-1(2H)-yl)acetaldehyde.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionwere added an aqueous saturated sodium hydrogen carbonate solution and ethyl acetate
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted 5 times with ethyl acetate
  6. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-854cfc879d3042f1aed75489290203ef
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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