Ethyl 4-(6-oxo-1,6-dihydropyridin-3-yl)benzoate → HCID 18617476, Verbindung

HRID 1264241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264241
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH:4]=[CH:3]1>CC(O)=O>[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Komponenten

3

Edukt 1

HCID 18617564Ethyl 4-(6-oxo-1,6-dihydropyridin-3-yl)benzoate

Produkt 1

HCID 18617476HCID 18617476, VerbindungAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Ethyl 4-(6-oxo-1,6-dihydro-pyridin-3-yl)-benzoate (450 mg, 1.8 mmol) (reference example 36f) is dissolved in HOAc (15 mL), and the the solution is degassed several times by alternating N2/vacuum. 50 mg of PtO2 is added and the mixture is degassed for several minutes before being placed under a H2 atmosphere. The mixture is stirred at room temperature for 9 hours then degassed several times by alternating N2/vacuum then filtered through a plug of celite. The plug is washed thoroughly with HOAc and the filtrate concentrated. The residue is chromatographed first on silica gel (3% MeOH/CH2Cl2), and then by Reverse-Phase HPLC to afford 330 mg of the title compound (72%) as a white solid. 1H NMR (CDCl3) δ 1.39 (t, J=7 Hz, 3H), 2.12 (m, 2H), 2.56 (m, 2H), 3.13 (m, 1H), 3.41 (dd, J=11.3, 11.3, 1H), 3.53 (m, 1H), 4.37 (q, J=7, 2H), 6.78 (bs, 1H), 7.16 (d, J=8 Hz, 2H), 8.01 (d, J=8 Hz, 2H). MS (Ion spray) m/z 248 (M+H)+.

Aufarbeitung

  1. customthe the solution is degassed several times
  2. addition50 mg of PtO2 is added
  3. customthe mixture is degassed for several minutes
  4. customthen degassed several times
  5. filtrationthen filtered through a plug of celite
  6. washThe plug is washed thoroughly with HOAc
  7. concentrationthe filtrate concentrated
  8. customThe residue is chromatographed first on silica gel (3% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-185489f366a24404a13edd9afa51747a
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541505B1

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