Trifluoroacetic acid → (7-(1H-imidazol-1-yl)-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

HRID 385553Notes

Reaction equation

HRID 385553 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)[CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:22].FC(F)(F)C(O)=O>>[N:17]1([C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[CH:9][C:8](=[O:22])[N:7]3[CH2:6][CH:2]=[O:1])=[N:12][CH:13]=2)[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57815179HCID 57815179, compound

Product 1

HCID 57815312(7-(1H-imidazol-1-yl)-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehydeYield 117.3%

Conditions

Temperature
55 °C

Procedure

To 0.12 g of 1-((1,3-dioxolan-2-yl)methyl)-7-(1H-imidazol-1-yl)-1,5-naphthyridin-2(1H)-one, 2 mL of an 80% aqueous trifluoroacetic acid solution was added at room temperature, and the mixture was stirred at 50 to 60° C. for 1 hour 30 minutes. The reaction mixture was cooled to room temperature, and the solvent was then distilled off under reduced pressure. The resultant residue was charged with chloroform and water and adjusted to pH 7.8 with a 20% aqueous sodium hydroxide solution. The organic layer was separated and the aqueous layer was extracted with chloroform, and then further extracted with ethyl acetate. 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 0.12 g of (7-(1H-imidazol-1-yl)-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationthe solvent was then distilled off under reduced pressure
  3. additionThe resultant residue was charged with chloroform and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with chloroform
  6. extractionfurther extracted with ethyl acetate
  7. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0dc340e34777481d89571a371d584283
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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