Trifluoroacetic acid → HCID 59398064, compound

HRID 39837Notes

Reaction equation

HRID 39837 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)[CH:15]=2)[C:10]([CH3:22])=[CH:9][C:8]1=[O:23].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[N:17]1([C:14]2[CH:15]=[C:16]3[C:11]([C:10]([CH3:22])=[CH:9][C:8](=[O:23])[N:7]3[CH2:6][CH:2]=[O:1])=[CH:12][CH:13]=2)[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 593979121-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one

Product 1

HCID 59398064HCID 59398064, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 70 mg of 1-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one, 2 mL of 80% aqueous trifluoroacetic acid solution, was added, and stirred at room temperature for 1 hour, thereafter allowed to stand at room temperature for 14 hours. Ethyl acetate was added, neutralized with aqueous saturated sodium hydrogen carbonate solution, ethyl acetate was added, the organic layer was separated, and the aqueous layer was extracted 3 times with ethyl acetate. The organic layer and extracts were combined, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give (7-(1H-imidazol-1-yl)-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde as a white solid.

Workup

  1. waitto stand at room temperature for 14 hours
  2. additionwas added
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted 3 times with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-723126658272445ba9daee84ded82e00
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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