Trifluoroacetic acid → 2-Oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylic acid

HRID 347541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347541
[O:1]=[C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[OH-].[Na+].C(O)(C(F)(F)F)=O>CO>[O:1]=[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 21081726Methyl 2-oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylate

Produkt 1

HCID 210815862-Oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylic acidAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-oxo-1-(pyridin-2-yl)-1,2-dihydropyridine-3-carboxylate (500 mg, 2.17 mmol) and 3 N NaOH (1 mL) and methanol (10 mL) was stirred at rt overnight. To the reaction was added TFA (0.5 mL) and the mixture was concentrated in vacuo. The residue was dissolved in water (3 mL) and i-PrOH (10 mL). The solid which formed was filtered, washed with a small amount of water and i-PrOH, and dried to obtain the acid (260 mg, 55%) as a white solid. 1H NMR (DMF-d7) δ 14.14 (br s, 1H), 8.72 (d, 1H, J=4.9 Hz), 8.62 (dd, 1H, J=7.7, 2.2 Hz), 8.47 (dd, 1H, J=6.6, 2.2 Hz), 8.18–7.98 (m, 2H), 7.67 (dd, 1H, J=7.2, 5.3 Hz), 6.97 (t, 1H, J=6.6 Hz); MS(ESI+) m/z 217.2 (M+H)+.

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in water (3 mL)
  3. customThe solid which formed
  4. filtrationwas filtered
  5. washwashed with a small amount of water and i-PrOH
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-448b9c9d74ca4854962652a010be403d
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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