Trifluoroacetic acid → HCID 57815268, compound

HRID 385626Notes

Reaction equation

HRID 385626 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][N:13]=[CH:14][CH: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](=[CH:15][CH:14]=[N:13][CH:12]=2)[N:7]1[CH2:6][CH:2]=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 578152901-(1,3-dioxolan-2-ylmethyl)-1,6-naphthyridin-2(1H)-one

Product 1

HCID 57815268HCID 57815268, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.60 g of 1-(1,3-dioxolan-2-ylmethyl)-1,6-naphthyridin-2(1H)-one, 6 mL of a 90% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at room temperature for 12 hours. Thereto was added 1.0 mL of water, and the mixture was stirred for 1 hour, and stirred at 55 to 75° C. for 3 hours 30 minutes. The solvent was distilled off under reduced pressure, thereto were added a saturated aqueous sodium hydrogen carbonate solution and chloroform, and the mixture was stirred at room temperature for 1 hour 30 minutes. The organic layer was then separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain (2-oxo-1,6-naphthyridin-1(2H)-yl)acetaldehyde.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringstirred at 55 to 75° C. for 3 hours 30 minutes
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionwere added a saturated aqueous sodium hydrogen carbonate solution and chloroform
  5. stirringthe mixture was stirred at room temperature for 1 hour 30 minutes
  6. customThe organic layer was then separated
  7. extractionthe aqueous layer was extracted with chloroform
  8. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9a9436e802d74492840ba323550325b2
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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