Hydrazine hydrate (1:1) → HCID 13127486, compound

HRID 1462144Notes

Reaction equation

HRID 1462144 reaction equation
[CH2:1]([C:4]1[C:9]([F:10])=[C:8]([F:11])[C:7](F)=[C:6]([F:13])[C:5]=1[F:14])[CH:2]=[CH2:3].O.[NH2:16][NH2:17]>C(O)C>[CH2:1]([C:4]1[C:9]([F:10])=[C:8]([F:11])[C:7]([NH:16][NH2:17])=[C:6]([F:13])[C:5]=1[F:14])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 74435Allylpentafluorobenzene

Product 1

HCID 13127486HCID 13127486, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Allylpentafluorobenzene [41.6 g; described by Harper et al, J. Org. Chem., 29, 2385 (1964)] was added to a solution of hydrazine hydrate (100 ml) in ethanol (150 ml) and the mixture was heated at reflux for 24 hours. The solid precipitate which formed was collected by filtration and washed with ethanol and hexane to give 4-allyl-2,3,5,6-tetrafluorophenylhydrazine (18.8 g), m.p. 82°-84° C., in the form of colourless crystals. The filtrate was evaporated to dryness and the yellow solid thus obtained was washed with ethanol and hexane to give a further quantity (22.0 g) of 4-allyl-2,3,5,6-tetrafluorophenylhydrazine, m.p. 79°-81° C., in the form of a cream-coloured solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 24 hours
  3. customThe solid precipitate which formed
  4. filtrationwas collected by filtration
  5. washwashed with ethanol and hexane

Sources & evidence

ORD record
ord-9eddc457912746e7981727a73c3dfaa1
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

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