Nitric Acid → 2-Bromo-6-methyl-4-nitro-1-oxo-1lambda~5~-pyridine

HRID 1775372

Reaktionsgleichung

Reaktionsgleichung von HRID 1775372
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N+:7]=1[O-:13]>S(=O)(=O)(O)O>[Br:5][C:6]1[CH:11]=[C:10]([N+:1]([O-:4])=[O:2])[CH:9]=[C:8]([CH3:12])[N+:7]=1[O-:13]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 36520842-Bromo-6-methylpyridine 1-oxide

Produkt 1

HCID 27518162-Bromo-6-methyl-4-nitro-1-oxo-1lambda~5~-pyridineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To cooled nitric acid (concentrated, 168 ml) was added sulfuric acid (concentrated, 300 ml) under cooling followed by 2-bromo-6-methyl-pyridine 1-oxide (35 g, 0.186 mol). The mixture was stirred at 70° C. for 4 hours, cooled to room temperature and poured slowly on crushed ice. A stream of nitrogen was bubbled through the mixture overnight. The mixture was basified to pH 8 under cooling with NaOH (10N, ca. 1 L), diluted with water (3 L) and extracted with DCM (5×). The combined organic phases were dried (sodium sulfate) and evaporated to dryness to yield 27.6 g of a yellow crystalline solid (0.118 mol, 57%).

Aufarbeitung

  1. temperatureunder cooling
  2. temperaturecooled to room temperature
  3. additionpoured slowly
  4. customon crushed ice
  5. customA stream of nitrogen was bubbled through the mixture overnight
  6. temperatureunder cooling with NaOH (10N, ca. 1 L)
  7. additiondiluted with water (3 L)
  8. extractionextracted with DCM (5×)
  9. dry with materialThe combined organic phases were dried (sodium sulfate)
  10. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e287d211fc624e4b86179e7e74eb4be1
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260441B2

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