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

HRID 385494Notes

Reaction equation

HRID 385494 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[N:14][CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:17].FC(F)(F)C(O)=O>>[O:17]=[C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][N:14]=[CH:13][CH:12]=2)[N:7]1[CH2:6][CH:2]=[O:1]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid3×HCID 578152341-((1,3-Dioxolan-2-yl)methyl)-1,7-naphthyridin-2(1H)-one

Product 1

HCID 578151862-(2-oxo-1,7-naphthyridin-1(2H)-yl)acetaldehydeYield 99.5%

Conditions

Temperature
75 °C

Procedure

To 3.1 g of 1-(1,3-dioxolan-2-ylmethyl)-1,7-naphthyridin-2(1H)-one, 30 mL of an 80% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at 70 to 80° C. for 2 hours. The reaction mixture was cooled to room temperature, then 30 mL of an 80% aqueous trifluoroacetic acid solution was added thereto, the mixture was stirred at 70 to 80° C. for 3 hours 30 minutes, and the temperature was increased to 75 to 85° C. and the mixture was stirred for 2 hours. Thereto was further added 30 mL of an 80% aqueous trifluoroacetic acid solution, and the mixture was stirred at 80 to 90° C. for 2 hours 30 minutes. The reaction mixture was cooled to room temperature, and then left overnight. The solvent was distilled off under reduced pressure, and the resultant residue was charged with chloroform and water and adjusted to pH 10.4 with a 20% aqueous sodium hydroxide solution. Sodium chloride was added thereto, 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 dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.5 g of (2-oxo-1,7-naphthyridin-1(2H)-yl)acetaldehyde as a yellow oily substance.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at 70 to 80° C. for 3 hours 30 minutes
  3. temperaturethe temperature was increased to 75 to 85° C.
  4. stirringthe mixture was stirred for 2 hours
  5. stirringthe mixture was stirred at 80 to 90° C. for 2 hours 30 minutes
  6. temperatureThe reaction mixture was cooled to room temperature
  7. waitleft overnight
  8. distillationThe solvent was distilled off under reduced pressure
  9. additionthe resultant residue was charged with chloroform and water
  10. additionSodium chloride was added
  11. customthe organic layer was separated
  12. extractionthe aqueous layer was extracted with chloroform
  13. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  14. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-102520337149420c93c282ac1e7947d4
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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