Trifluoroacetic acid → (7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehyde

HRID 385510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385510
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[N:15]=2)[CH:10]=[CH:9][C:8]1=[O:19].FC(F)(F)C(O)=O>O>[CH3:18][O:17][C:14]1[N:15]=[C:16]2[C:11]([CH:10]=[CH:9][C:8](=[O:19])[N:7]2[CH2:6][CH:2]=[O:1])=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 578153441-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one

Produkt 1

HCID 57815463(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehydeAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
66 °C

Versuchsvorschrift

To 2.8 g of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one, 20 mL of an 80% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at 60 to 72° C. for 3 hours 20 minutes, and at 80 to 85° C. for 2 hours 20 minutes, 4 mL of water was then added thereto and the mixture was further stirred for 4 hours. The reaction mixture was cooled to room temperature and then left overnight, and the solvent was distilled off under reduced pressure. To the resultant residue, a saturated aqueous sodium hydrogen carbonate solution 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 dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.8 g of (7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehyde as a yellow solid.

Aufarbeitung

  1. stirringthe mixture was further stirred for 4 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. waitleft overnight
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the resultant residue, a saturated aqueous sodium hydrogen carbonate solution and chloroform were added
  6. customthe organic layer was 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

Quellen und Nachweise

ORD-Eintrag
ord-35f0aee96f7847838b4cb16ac581186a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367831B2

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