Potassium Hydroxide → HCID 21717332, Verbindung

HRID 1386094

Reaktionsgleichung

Reaktionsgleichung von HRID 1386094
[OH-].[K+].[OH:3][C:4]1[C:5]([N+:11]([O-:13])=[O:12])=[N:6][CH:7]=[C:8]([CH3:10])[CH:9]=1.[K].[CH3:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18]Cl>C(O)C>[CH3:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18][O:3][C:4]1[C:5]([N+:11]([O-:13])=[O:12])=[N:6][CH:7]=[C:8]([CH3:10])[CH:9]=1

Komponenten

6

Edukt 4

HCID 14797Potassium Hydroxide2×HCID 2211542,6-Dimethylbenzyl Chloride2×HCID 5462222PotassiumHCID 217660195-Methyl-2-nitropyridin-3-ol

Produkt 1

HCID 21717332HCID 21717332, VerbindungAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

To 0.52 g (8.02 mmol) of 87% KOH and 0.15 g q-iodide in 6 ml 95% ethanol was added a solution of 3-hydroxy-5-methyl-2-nitropyridine (1.2 g, 7.79 mmol) in 25 ml of ethanol. To the resulting suspension of the potassium salt was added dropwise a solution of 2,6-dimethyl benzylchloride (1.24 g, 8.02 mmol) in 13 ml of ethanol. The reaction mixture was refluxed for 1 h. More 87% KOH (0.16 g) and 2,6-dimethylbenzylchloride (0.38 g) were added. The reaction mixture was refluxed for additional 70 min. The mixture was filtered and the inorganic salts were washed with ethanol and methylene chloride. The organic layer was evaporated in vacuo. The residue was dissolved in methylene chloride, washed with aqueous NaHCO3, dried and evaporated in vacuo. The residue was suspended in ether/isopropanol and filtered to give 1.72 g (81%) of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. temperatureThe reaction mixture was refluxed for additional 70 min
  3. filtrationThe mixture was filtered
  4. washthe inorganic salts were washed with ethanol and methylene chloride
  5. customThe organic layer was evaporated in vacuo
  6. dissolutionThe residue was dissolved in methylene chloride
  7. washwashed with aqueous NaHCO3
  8. customdried
  9. customevaporated in vacuo
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-75f2cc39dc7a474190888369be86b8ef
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265415B1

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