Trifluoroacetic acid → (2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehyde

HRID 385502Notes

Reaction equation

HRID 385502 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[CH:10]=[CH:9][C:8]1=[O:17].FC(F)(F)C(O)=O>O>[O:17]=[C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[N:15][CH:14]=[CH:13][CH:12]=2)[N:7]1[CH2:6][CH:2]=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 578152061-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 57815222(2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehydeYield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 1.1 g of 1-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one, 11 mL of a 90% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at room temperature for 2 hours. Then, 1.1 mL of water was added thereto and the mixture was stirred for 13 hours, and thereto was further added 1.1 mL of water and the mixture was stirred for 3 hours 30 minutes, and stirred at 50 to 70° C. for 1 hour 30 minutes. The solvent was distilled off under reduced pressure, and to the resultant residue, a saturated aqueous sodium hydrogen carbonate solution, water and chloroform were added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.75 g of (2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehyde as a yellow solid.

Workup

  1. stirringthe mixture was stirred for 13 hours
  2. stirringthe mixture was stirred for 3 hours 30 minutes
  3. stirringstirred at 50 to 70° C. for 1 hour 30 minutes
  4. distillationThe solvent was distilled off under reduced pressure
  5. additionto the resultant residue, a saturated aqueous sodium hydrogen carbonate solution, water and chloroform were added
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with chloroform
  8. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bd2ab88a4a9042339d93c64539b1d88b
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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