Dimethyl Sulfoxide → 6-hydroxypyridazine-3-carboxylic acid

HRID 131296

Reaktionsgleichung

Reaktionsgleichung von HRID 131296
[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.Br.C(O)(=O)C.CS(C)=O>C(O)(=O)C>[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]([OH:10])=[O:9])[CH:4]=[CH:3]1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 996211,4,5,6-Tetrahydro-6-oxo-3-pyridazinecarboxylic acidHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Produkt 1

HCID 3059706-hydroxypyridazine-3-carboxylic acidAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid (20 g) in acetic acid (50 mL) is added 25% hydrobromic acid/acetic acid (200 mL) and thereto is added dropwise dimethylsulfoxide (22.0 g) at room temperature. The mixture is stirred at room temperature for 3 days. The resultant precipitates are collected by filtration, washed successively with acetic acid and water and dried at 40° C. overnight to give 6-oxo-1,6-dihydropyridazine-3-carboxylic acid (10.55 g, yield; 54%) as colorless crystals. MS (ESI) m/z: 139 [M−H]−

Aufarbeitung

  1. customThe resultant precipitates
  2. filtrationare collected by filtration
  3. washwashed successively with acetic acid and water
  4. customdried at 40° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-e94ef1afdff847aa87dcc79ed74fcb72
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384952B2

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