Nitric Acid → 5,6-Dimethyl-3-nitro-1,2-dihydropyridin-2-one

HRID 1994233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994233
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5](=[O:9])[NH:6][C:7]=1[CH3:8]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 1197855,6-Dimethyl-2-pyridone

Produkt 1

HCID 2646205,6-Dimethyl-3-nitro-1,2-dihydropyridin-2-oneAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

5,6-Dimethyl-2-pyridone (1-013-03) (3.695 g) was dissolved in conc. sulfuric acid (38 mL) under ice-cooling, and the reaction mixture was stirred under ice-cooling, and then to the reaction mixture was added dropwise 70% nitric acid (3.53 mL) at 3 to 5° C. as internal temperature for 50 min, and then the reaction mixture was stirred. After 2 h, the reaction mixture was poured gradually into ice and the resulting crystal was filtered. The crystal was washed with water to give 5,6-dimethyl-3-nitro-2-pyridone (1-013-04) (3.102 g, 61.5%, m.p.: 251-257 (dec)). Furthermore the aqueous layer was extracted five times with chloroform, the organic layer was dried over magnesium sulfate, and evaporated under reduced pressure. The resulting crystal was filtered to give an additional 5,6-dimethyl-3-nitro-2-pyridone (1-013-04)(271 mg, 5.4%).

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe reaction mixture was stirred
  4. additionthe reaction mixture was poured gradually into ice
  5. filtrationthe resulting crystal was filtered
  6. washThe crystal was washed with water

Quellen und Nachweise

ORD-Eintrag
ord-abf1bb2285e945da966e111648ba5945
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652141B2

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