Hydrazine hydrate (1:1) → (Z)-7-Aminohept-5-enoic Acid

HRID 358624Notes

Reaction equation

HRID 358624 reaction equation
O.NN.C1(=O)[N:8]([CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])C(=O)C2=CC=CC=C12>C(O)C.O>[NH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67946768(Z)-7-Phthalimidohept-5-enoic Acid

Product 1

HCID 86744642(Z)-7-Aminohept-5-enoic AcidYield 112.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydrazine hydrate (0.19 ml) was added to a solution of (Z)-7-phtalimidohept-5-enoic acid (1.05 g) in ethanol (25 ml) and water (5 ml). The solution was refluxed for 3 hours and then the solvent was removed. The residue was suspended in water and the pH of the solution was adjusted to 5. The resulting precipitate was collected by filtration. The filtrate was evaporated to dryness and extracted with ethanol. The ethanol extracts were evaporated to dryness to give the title compound as an oil (0.62 g).

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. customthe solvent was removed
  3. filtrationThe resulting precipitate was collected by filtration
  4. customThe filtrate was evaporated to dryness
  5. extractionextracted with ethanol
  6. customThe ethanol extracts were evaporated to dryness

Sources & evidence

ORD record
ord-8e756c3c47864deebc89d4eb381cda53
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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