N-(2-(benzyloxy)phenyl)-3-fluoroisonicotinamide → 3-fluoro-N-(2-hydroxyphenyl)isonicotinamide

HRID 718041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 718041
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[F:23])C1C=CC=CC=1>Br.CC(O)=O.O.C(=O)(O)[O-].[Na+]>[F:23][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[OH:8])=[O:24]

Komponenten

6

Edukt 1

HCID 59783597N-(2-(benzyloxy)phenyl)-3-fluoroisonicotinamide

Produkt 1

HCID 597834993-fluoro-N-(2-hydroxyphenyl)isonicotinamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 260Hydrogen BromideLösungsmittelHCID 962WaterLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Title compound 24 (4.40 g, 13.6 mmol) was dissolved in 33% HBr in AcOH (30 mL) and the reaction mixture was stirred at room temperature for 2 hours. The mixture was diluted with water and solid sodium bicarbonate (until alkaline) then extracted twice with ethyl acetate. The combined organic extracts were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The crude was triturated in 30% ethyl acetate in hexanes to afford the title compound 25 (2.36 g, 75%) as a beige solid. LRMS (ESI): (calc) 232.06. (found) 233.1 (MH)+.

Aufarbeitung

  1. extractionthen extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude was triturated in 30% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3df4b7fd99bc47faa230ce973e2eac64
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193749B2

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