Hydrazine hydrate (1:1) → HCID 86737843, compound

HRID 1277484Notes

Reaction equation

HRID 1277484 reaction equation
C1(=O)[N:5]([CH2:6][C:7]([NH:9][C:10]([CH3:18])([CH3:17])[CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:8])C(=O)C2=CC=CC=C12.O.NN.[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(O)C.CCOCC>[CH2:7]([O-:8])[CH3:6].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([O-:33])=[O:32].[NH2:5][CH2:6][C:7]([NH:9][C:10]([CH3:18])([CH3:17])[CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:8]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 444972Fumaric AcidHCID 23454140HCID 23454140, compound

Product 1

HCID 86737843HCID 86737843, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 2-phthalimido-N-(1,1-dimethyl-2-cyclopentylethyl)acetamide (15.8 g, 48.2 mmol) in ethanol (50 ml) was treated with hydrazine hydrate (2.65 g, 53.0 mmol) and the mixture heated under reflux for 1 hour. After cooling and allowing to stand at 0° for 24 hours, the slurry was filtered and the residue washed with petrol (40°-60°) (2×25 ml). The combined filtrates were evaporated to dryness and thecolourless oily residue triturated with petrol (40°-60°, 100 ml). The insoluble material was filtered off and the filtrate evaporated to dryness giving a colourless oil. The oil was dissolved in ethanol (30 ml) and treated with a hot solution of fumaric acid (5.9 g) in ethanol (80ml). On diluting with ether (100 ml) and cooling, colourless plates were deposited, m.p. 159°-160°. Found: C, 56.75; H, 8.78; N, 7.89; C11H22N2O.C4H4O4C2H5OH requires C, 56.67; H, 8.89; N, 7.78.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe slurry was filtered
  5. washthe residue washed with petrol (40°-60°) (2×25 ml)
  6. customThe combined filtrates were evaporated to dryness and thecolourless oily residue
  7. customtriturated with petrol (40°-60°, 100 ml)
  8. filtrationThe insoluble material was filtered off
  9. customthe filtrate evaporated to dryness
  10. customgiving a colourless oil
  11. temperaturecooling

Sources & evidence

ORD record
ord-4860455795144c93a18609f9b53719c6
Source dataset
uspto-grants-1981_07
Patent number
US04277498

Reaction notes

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