Hydrochloric Acid → HCID 20253304, compound

HRID 461972Notes

Reaction equation

HRID 461972 reaction equation
[CH:1]1(ON2C(=O)C3=CC=CC=C3C2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:18].NN.Cl>C(O)C>[CH:1]1([CH:4]2[CH:5]=[CH:1][CH:2]=[CH:3][O:18]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 102632872-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 20253304HCID 20253304, compoundYield 175.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-cyclopentyloxyphthalimide (11 g), 100% hydrazine hydrate (2.6 g), and ethanol (30 ml) was heated under reflux for 5 minutes. Concentrated hydrochloride acid (6 ml) was added to the mixture, which was heated under reflux Water (20 ml) was added to the mixture, which was cooled to room temperature, and filtered. The filtrate was evaporated to dryness, ethanol (50 ml) was added to the residue, and a small amount of insoluble material was filtered off. The filtrate was evaporated to dryness, and the residue was recrystallised from ethanol/ether to give cyclopentyloxamine (6.28 g,) 96%), m.p. 156.9°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 minutes
  3. temperaturewas heated under reflux Water (20 ml)
  4. additionwas added to the mixture, which
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness, ethanol (50 ml)
  7. additionwas added to the residue
  8. filtrationa small amount of insoluble material was filtered off
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-e22c48017825466f9565eeb95fc61372
Source dataset
uspto-grants-1977_12
Patent number
US04064346

Reaction notes

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