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

HRID 39690Notes

Reaction equation

HRID 39690 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-18bba5ec4e5647d6803d7058695a05b9
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

Loading…