Acetic Acid → 1-(4-Amino-2-fluoro-phenyl)-2,3-dihydro-1H-pyridin-4-one

HRID 723898

Reaktionsgleichung

Reaktionsgleichung von HRID 723898
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH:16]=[CH:15][C:14](=[O:17])[CH2:13][CH2:12]1.C(O)(=O)C.[H][H]>C1COCC1.[Pd].C([O-])([O-])=O.[Ca+2]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH:12]=[CH:13][C:14](=[O:17])[CH2:15][CH2:16]2)=[C:2]([F:1])[CH:7]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 218776411-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 218778771-(4-Amino-2-fluoro-phenyl)-2,3-dihydro-1H-pyridin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 12000666Calcium Palladium CarbonateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 500 ml Parr bottle, 1-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-one (Step 3, 35 g, 148.3 mmol), Pd/CaCO3 (3.5 g, 10 wt %) and acetic acid (17 ml, 297 mmol) are combined in THF (350 ml). The mixture is hydrogenated at 40° C. under 15 psi hydrogen for 6 h at which time the reaction is complete by HPLC. The reaction mixture is filtered through a GF/F filter and the catalyst cake washed with THF (350 ml). The filtrate is partitioned between 500 ml of NaHCO3 and 500 ml of ethyl acetate. The organic layer is washed again with 500 ml of NaHCO3. The organic layer is separated and dried over MgSO4. The mixture is filtered, and the filtrate is concentrated under reduced pressure to afford 29.0 g (95% recovery) of the title compound, MS (ESI−) for C11H11FN2O m/z 205.0 (M−H)−; 1H NMR (MeOD) δ 7.37 (d, 1H), 7.02 (t, 1H), 6.47 (m, 3H), 5.07 (d, 1H), 3.84 (t, 2H), 2.58 (t, 1H).

Aufarbeitung

  1. filtrationThe reaction mixture is filtered through a GF/F
  2. filtrationfilter
  3. washthe catalyst cake washed with THF (350 ml)
  4. customThe filtrate is partitioned between 500 ml of NaHCO3 and 500 ml of ethyl acetate
  5. washThe organic layer is washed again with 500 ml of NaHCO3
  6. customThe organic layer is separated
  7. dry with materialdried over MgSO4
  8. filtrationThe mixture is filtered
  9. concentrationthe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-374ade24a4084819800093cf56ece0fc
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141588B2

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