Acetic Acid → 2-[[4-(Methylthio)phenyl]amino]isonicotinic acid

HRID 452631

Reaktionsgleichung

Reaktionsgleichung von HRID 452631
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[CH3:11][S:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.[H-].[Na+].C(O)(=O)C>CN(C)C=O>[CH3:11][S:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=2)[C:5]([OH:7])=[O:6])=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 660384-(Methylthio)anilineHCID 3453602-Fluoroisonicotinic acid

Produkt 1

HCID 284003552-[[4-(Methylthio)phenyl]amino]isonicotinic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 2-fluoroisonicotinic acid (620 mg, 4.95 mmol) and 4-(methylthio)aniline (0.984 mL, 8.42 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (792 mg, 19.8 mmol), and the resulting mixture was stirred under an argon atmosphere at 85° C. for 5 hr. After cooling, acetic acid (1.2 mL) was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Ethyl acetate and water were added to the residue, the mixture was stirred for 20 min, and the precipitate was collected by filtration to give crude 2-[[4-(methylthio)phenyl]amino]isonicotinic acid.

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionEthyl acetate and water were added to the residue
  4. stirringthe mixture was stirred for 20 min
  5. filtrationthe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-421b9b0c69434c2cabddaf72f72d3971
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492378B2

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