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

HRID 631834

Reaktionsgleichung

Reaktionsgleichung von HRID 631834
[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 poored 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 crystaline solid (0.118 mol, 57%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-970edf86b814412faf18b6f7474e2814
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321724B2

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