Hydrazine hydrate (1:1) → HCID 178514324, compound

HRID 1382805Notes

Reaction equation

HRID 1382805 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.O.[NH2:14][NH2:15]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:14][NH2:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 872035-chloro-1H-indole-2,3-dione

Product 1

HCID 178514324HCID 178514324, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred slurry of 100 g (0.55 mol) of 5-chloroisatin in 930 ml of ethanol was added 40 ml (0.826 mol) of hydrazine hydrate, resulting in a red solution. The solution was heated under reflux for 3.5 hours, during which time a precipitate appeared. The reaction mixture was stirred overnight, and then the precipitate was recovered by filtration to give 5-chloro-3-hydrazono-2-oxindole as a yellow solid, which was dried in a vacuum oven. The dried solid weighed 105.4 g.

Workup

  1. customresulting in a red solution
  2. temperatureThe solution was heated
  3. temperatureunder reflux for 3.5 hours, during which time a precipitate
  4. filtrationthe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-18dd96305bbb452f97a1b01d7fba98fe
Source dataset
uspto-grants-1989_02
Patent number
US04808601

Reaction notes

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