(3-chloro-6-oxopyridazin-1(6H)-yl)acetic acid → 2-(6-Oxo-1,6-dihydropyridazin-1-yl)acetic acid

HRID 1888172

Reaktionsgleichung

Reaktionsgleichung von HRID 1888172
Cl[C:2]1[CH:7]=[CH:6][C:5](=[O:8])[N:4]([CH2:9][C:10]([OH:12])=[O:11])[N:3]=1>CO.[Pd]>[O:8]=[C:5]1[N:4]([CH2:9][C:10]([OH:12])=[O:11])[N:3]=[CH:2][CH:7]=[CH:6]1

Komponenten

4

Edukt 1

HCID 5121297(3-chloro-6-oxopyridazin-1(6H)-yl)acetic acid

Produkt 1

HCID 14155362-(6-Oxo-1,6-dihydropyridazin-1-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of [3-chloro-6-oxopyridazin-1(6H)-yl]acetic acid (1.00 g, 5.30 mmol) in methanol (40 ml) was added 100 mg of 10% Pd/C. After the reaction mixture was stirred at ambient temperature under a hydrogen balloon for 1 h, the palladium was filtered off through Celite®. The filtrate was concentrated in vacuo and purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). Removal of the volatiles in vacuo afforded the title compound as a white crystalline solid. 1H NMR (D2O) δ: 8.06 (dd, J=3.9, 1.4 Hz, 1H), 7.56 (dd, J=9,4, 3.9 Hz, 1H), 7.12 (dd, J=9.4, 1.5 Hz, 1H), 4.95 (s, 2H). LC/MS 155.2 (M+1)+.

Aufarbeitung

  1. filtrationthe palladium was filtered off through Celite®
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)
  4. customRemoval of the volatiles in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a1a6c7df90284f45ba9fcc7cfd920f50
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501786B2

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