Hydrazine → HCID 178518904, compound

HRID 2357513Notes

Reaction equation

HRID 2357513 reaction equation
C([N:5]1[CH:13](O)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:15])[CH:11]=2)[C:6]1=[O:16])(C)(C)C.[NH2:17]N>C(O)(=O)C>[Cl:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[C:6]([OH:16])=[N:17][N:5]=[CH:13]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 251930612-Tert-butyl-5-chloro-3-hydroxyisoindolin-1-one

Product 1

HCID 178518904HCID 178518904, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 2-tert-butyl-5-chloro-3-hydroxyisoindolin-1-one (5.26 g, 21.9 mmol) in glacial acetic acid (32 mL) was heated with stirring until the mixture became a clear solution. Anhydrous hydrazine (1.0 mL, 22 mmol) was added dropwise and the resultant solution was stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure. Water was added to the mixture, after which a solid material precipitated out of the solution. The solid was collected by filtration and rinsed thoroughly with water, followed by air-drying to afford 6-chlorophthalazin-1-ol (3.9 g, 98% yield) as an off-white powder (mp 271-273° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater was added to the mixture
  5. customafter which a solid material precipitated out of the solution
  6. filtrationThe solid was collected by filtration
  7. washrinsed thoroughly with water
  8. customby air-drying

Sources & evidence

ORD record
ord-1cc79bce83f54b89a8aef1d1ae90c871
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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