Hydrazine hydrate (1:1) → 2,3-Dihydrophthalazine-1,4(5H,8H)-dione

HRID 42222Notes

Reaction equation

HRID 42222 reaction equation
[C:1]1(=O)[C:9]2[CH2:8][CH:7]=[CH:6][CH2:5][C:4]=2[C:3](=[O:10])[O:2]1.O.[NH2:13][NH2:14]>C1(C)C=CC=CC=1>[C:3]1(=[O:10])[C:4]2[CH2:5][CH:6]=[CH:7][CH2:8][C:9]=2[C:1](=[O:2])[NH:14][NH:13]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1383481,4-Cyclohexadiene-1,2-dicarboxylic anhydride

Product 1

HCID 574716262,3-Dihydrophthalazine-1,4(5H,8H)-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of isobenzofuran-1,3(4H,7H)-dione (4.2 g, 28 mmol) in 45 mL toluene was heated at reflux and charged with hydrazine hydrate (1.63 mL, 33.6 mmol) dropwisely in a round bottom flask equipped with a condenser. The reaction mixture was heated at reflux for 2 h. The mixture was filtered to afford the titled compound a white solid (4.2 g, yield: 91%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customequipped with a condenser
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 2 h
  6. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-905e9578a11f437282a67df6968f5e6f
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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