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

HRID 2187192Notes

Reaction equation

HRID 2187192 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 111481501,1-Dimethyl-2-(3-pyridylmethyl)hydrazineYield 20.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

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 (5° 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.

Workup

  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

Sources & evidence

ORD record
ord-b02f7976ca5e46f2b6ffc9df585b42e1
Source dataset
uspto-grants-2002_06
Patent number
US06407248B1

Reaction notes

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