Hydrazine hydrate (1:1) → 4-Phenylpyridazine-3,6-dione

HRID 1278561Notes

Reaction equation

HRID 1278561 reaction equation
[C:1]1([C:7]2[C:8](O[C:11](=[O:13])[CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O.O.C([O-])(=O)C.[Na+].O.[NH2:23][NH2:24]>C(O)(=O)C>[C:1]1([C:7]2[C:8](=[O:9])[N:23]=[N:24][C:11](=[O:13])[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 99174Phenylmaleic anhydrideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 184306814-Phenylpyridazine-3,6-dioneYield 33.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Phenylmaleic anhydride (20 g, 115 mmol), sodium acetate trihydrate (18.75 g, 138 mmol), hydrazine monohydrate (6.68 ml, 133 mmol) and 40% aqueous acetic acid (400 ml) were heated at reflux for 15 h then allowed to cool. The reaction mixture was left to cool in the fridge for 1h. The solid produced was filtered and washed with water and diethyl ether before drying in a vacuum oven at 40° C. to give the required product (7.26 g). 1H NMR (250 MHz, DMSO) 8 3.43 (2H, broad peak), 7.17 (1H, s), 7.44 (3H, m), 7.81 (2H, m); MS (ES+) m/e 189 [MH+].

Workup

  1. temperatureat reflux for 15 h
  2. temperatureto cool
  3. waitThe reaction mixture was left
  4. temperatureto cool in the fridge for 1h
  5. customThe solid produced
  6. filtrationwas filtered
  7. washwashed with water and diethyl ether
  8. custombefore drying in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-7b1885cc03ce48c4aff65fd4f0d94ab8
Source dataset
uspto-grants-2002_09
Patent number
US06444666B1

Reaction notes

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