8-Hydroxyquinoline → 8-hydrazinylquinoline

HRID 1414091Notes

Reaction equation

HRID 1414091 reaction equation
[NH2:1][NH2:2].O[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2>O.[Cl-].[Na+].O>[NH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)[NH2:2]

Participants

5

Reactant 2

HCID 19238-HydroxyquinolineHCID 9321Hydrazine

Product 1

HCID 5944338-hydrazinylquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of hydrazine in water (equivalent to 250 ml of 100% hydrazine hydrate) was added to the 8-hydroxyquinoline and the mixture was refluxed under nitrogen for 68 hours. After cooling to about 40° C., brine was added and the mixture was extracted with benzene. The benzene solution was washed once with brine, three times with Claisen's alkali (prepared by dissolving 35 g of potassium hydroxide in 25 ml of water, cooling, and adding 100 ml of methanol), twice again with brine, dried over magnesium sulfate, filtered and evaporated to give 60.0 g of an orange oil which crystallized on standing. IR and NMR analysis confirmed the product to be 8-hydrazinoquinoline.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 68 hours
  2. extractionthe mixture was extracted with benzene
  3. washThe benzene solution was washed once with brine, three times with Claisen's alkali (prepared by dissolving 35 g of potassium hydroxide in 25 ml of water, cooling, and adding 100 ml of methanol), twice again with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a3ff54e5290a466c81831cd75e018603
Source dataset
uspto-grants-1981_02
Patent number
US04252959

Reaction notes

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