Trifluoroacetic acid → (4-chloro-2-oxoquinolin-1(2H)-yl)acetaldehyde

HRID 2193098Notes

Reaction equation

HRID 2193098 reaction equation
FC(F)(F)C(O)=O.[O:8]1CCO[CH:9]1[CH2:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([Cl:24])=[CH:16][C:15]1=[O:25]>>[Cl:24][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]([CH2:13][CH:9]=[O:8])[C:15](=[O:25])[CH:16]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398226HCID 59398226, compound

Product 1

HCID 59398313(4-chloro-2-oxoquinolin-1(2H)-yl)acetaldehyde

Procedure

Into 3 mL of a 90% aqueous trifluoroacetic acid solution, 156 mg of 1-(1,3-dioxolan-2-ylmethyl)-4-chloroquinolin-2(1H)-one was dissolved, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the reaction mixture was alkalified with an aqueous saturated sodium hydrogen carbonate solution, and then extracted with ethyl acetate. The organic layer was washed sequentially with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 192 mg of a pale yellow oily substance, (4-chloro-2-oxoquinolin-1(2H)-yl)acetaldehyde.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed sequentially with water
  4. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6a9b386908e647458a8eadf4556e3913
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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