Hydrazine → 6-(1-Ethylcyclohexyl)pyridazin-3(2H)-one

HRID 648150Notes

Reaction equation

HRID 648150 reaction equation
[CH2:1]([C:3]1([C:9](=O)[CH:10]=[CH:11][C:12]([OH:14])=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:2].[NH2:16][NH2:17]>C(O)C>[CH2:1]([C:3]1([C:9]2[CH:10]=[CH:11][C:12](=[O:14])[NH:16][N:17]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 543762094-(1-Ethylcyclohexyl)-4-oxobut-2-enoic acid

Product 1

HCID 204821506-(1-Ethylcyclohexyl)pyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 14.0 g. of 4-(1-ethylcyclohexyl)-4-oxo-2-butenoic acid was added 100 ml. of ethanol and 4 g. of hydrazine. The mixture was stirred under reflux under a 300 watt sun-lamp in a 100 ml. Pyrex flask for 18 hours. The lamp was placed 5 cm. from the flask and emitted light of wave lengths primarily between 200 and 800 mμ. The mixture was then evaporated to dryness under vacuum, and to the residue was added 1000 ml. of diethyl ether. The ether solution was washed with 500 ml. of 0.1 N hydrochloric acid, 0.1 N sodium hydroxide and saturated sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum to an oil. The oil was taken up in a little hexane and triturated to obtain a crystalline solid. The solid was recrystallized from ethyl acetate/hexane to obtain 0.15 g. of the desired product, m.p. 138°-140°. It was identified by its infrared spectrum, showing absorption bands at 1650 and 1675 cm.-1, and by its mass spectroscopy spectrum, showing its molecular ion of mass 206.

Workup

  1. temperatureunder reflux under a 300 watt sun-lamp in a 100 ml
  2. customThe mixture was then evaporated to dryness under vacuum
  3. additionto the residue was added 1000 ml
  4. washThe ether solution was washed with 500 ml
  5. dry with materialof 0.1 N hydrochloric acid, 0.1 N sodium hydroxide and saturated sodium chloride solution, dried over magnesium sulfate
  6. customevaporated under vacuum to an oil
  7. customtriturated
  8. customto obtain a crystalline solid
  9. customThe solid was recrystallized from ethyl acetate/hexane
  10. customto obtain 0.15 g

Sources & evidence

ORD record
ord-45cbf66dea6547bba463ed131be65383
Source dataset
uspto-grants-1983_10
Patent number
US04411753

Reaction notes

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