Water → 1,1-Dimethyl-2-(3-pyridylmethyl)hydrazine

HRID 1457859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1457859
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:17])[N:9]=[CH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.O.[OH-].[Na+]>C(OCC)C>[CH3:7][N:8]([CH3:17])[NH:9][CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 311921Nicotinaldehyde dimethylhydrazoneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 111481501,1-Dimethyl-2-(3-pyridylmethyl)hydrazineAusbeute 20,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In 100 ml of dry ethyl ether was suspended 4.6 g of lithium aluminum hydride and with stirring in a nitrogen gas stream, a solution of 12.0 g of 1,1-dimethyl-2-(3-pyridylmethylidene)hydrazine in 50 ml of dry ethyl ether was added dropwise. The mixture was refluxed for 5 hours and, then, cooled (50° C.) and with stirring, 5 ml of water, 5 ml of 20% aqueous sodium hydroxide and 15 ml of water were added dropwise in succession. The insoluble matter was filtered off, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (eluent: chloroform-ethanol=10:1). The resulting oil was distilled under reduced pressure to give 2.5 g of the title compound as a yellow oil.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 5 hours
  2. stirringwith stirring
  3. filtrationThe insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (eluent: chloroform-ethanol=10:1)
  6. distillationThe resulting oil was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-79a6592dac354a5c8a16abf01f31418b
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849768

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