Trifluoroacetic acid → (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

HRID 2193094Notes

Reaction equation

HRID 2193094 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]=[C:21]([O:24][CH3:25])[CH:22]=2)[C:17]([CH3:26])=[CH:16][C:15]1=[O:27].C(=O)([O-])O.[Na+]>>[CH3:25][O:24][C:21]1[CH:22]=[C:23]2[C:18]([C:17]([CH3:26])=[CH:16][C:15](=[O:27])[N:14]2[CH2:13][CH:9]=[O:8])=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 593980471-(1,3-dioxolan-2-ylmethyl)-7-methoxy-4-methylquinolin-2(1H)-one

Product 1

HCID 59397837(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

Procedure

Into 2 mL of an 80% aqueous trifluoroacetic acid solution, 200 mg of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-4-methyl-2-oxo-1,2-dihydroquinoline was dissolved, and the mixture was stirred at room temperature for 11 hours. The reaction mixture was added with an aqueous saturated sodium hydrogen carbonate solution to be alkalified, and then extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a yellow oily substance, (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-efd219a3dec0418381493e1ab8f89810
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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