Nitric Acid → 2,6-Lutidine, 4-nitro-, 1-oxide

HRID 1640953

Reaktionsgleichung

Reaktionsgleichung von HRID 1640953
[N+:1]1([O-:9])[C:2]([CH3:8])=[CH:3][CH:4]=[CH:5][C:6]=1[CH3:7].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[N+:10]([C:4]1[CH:3]=[C:2]([CH3:8])[N+:1]([O-:9])=[C:6]([CH3:7])[CH:5]=1)([O-:12])=[O:11]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 140832,6-Dimethylpyridine N-oxide

Produkt 1

HCID 209452,6-Lutidine, 4-nitro-, 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A mixture of 2,6-lutidine 1-oxide (20, 15 g, 110 mmol) and concentrated sulfuric acid (98%, 30 ml) and concentrated nitric acid (70%, 12 ml) is heated under reflux for 3 hours. The mixture is poured into a large excess of ice and extracted with chloroform (3×100 ml). The combined chloroform extracts are washed with aqueous sodium hydroxide and water and dried over magnesium sulfate. Removal of the solvent yields pure yellow solid 4-Nitro-2,6-lutidine 1-oxide (21). 1H NMR (300 MHz, CDCl3) δ 2.64 (s, 6H), 8.08 (s, 2H). MS, m/z 169 (M+1), 210 (M+MeCN).

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. additionThe mixture is poured into a large excess of ice
  4. extractionextracted with chloroform (3×100 ml)
  5. washThe combined chloroform extracts are washed with aqueous sodium hydroxide and water
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-7093bf396e344b2baa5da26007741495
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114888B2

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