Trifluoroacetic acid → HCID 59398328, compound

HRID 2193199Notes

Reaction equation

HRID 2193199 reaction equation
FC(F)(F)C(O)=O.[O:8]1CCO[CH:9]1[CH2:13][N:14]1[C:23]2[C:18](=[C:19]([O:24][CH3:25])[CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]1=[O:26]>>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:18]=1[CH:17]=[CH:16][C:15](=[O:26])[N:14]2[CH2:13][CH:9]=[O:8]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59397941HCID 59397941, compound

Product 1

HCID 59398328HCID 59398328, compound

Procedure

To 15 mL of 80% aqueous trifluoroacetic acid solution, 0.44 g of 1-(1,3-dioxolan-2-ylmethyl)-5-methoxyquinolin-2(1H)-one was added, and stirred at room temperature for 5 hours. The solvent was removed under reduced pressure, ethyl acetate and water were added, the organic layer was separated, and sodium chloride was added to the aqueous layer, and extracted twice with ethyl acetate. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give (5-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde as a pale brown solid.

Workup

  1. customThe solvent was removed under reduced pressure, ethyl acetate and water
  2. additionwere added
  3. customthe organic layer was separated
  4. additionsodium chloride was added to the aqueous layer
  5. extractionextracted twice with ethyl acetate
  6. washwashed with aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-705bc8cb6c21470e9505493403e6e59a
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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