Acetic Acid → 5H,6H,7H,8H-pyrazino(2,3-d)pyridazine-5,8-dione

HRID 227755

Reaction equation

HRID 227755 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[C:7]([O:9][C:10](=[O:11])[C:2]=12)=O.O.[NH2:13][NH2:14].C(O)(=O)C>>[N:1]1[C:2]2[C:10](=[O:11])[NH:13][NH:14][C:7](=[O:9])[C:3]=2[N:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 78482Furo(3,4-b)pyrazine-5,7-dione

Product 1

HCID 8197895H,6H,7H,8H-pyrazino(2,3-d)pyridazine-5,8-dione

Procedure

The title compound was prepared according to a literature procedure (Paul, D. B. Aust. J Chem. 1974, 27, 1331). As described therein, 2,3-pyrazinedicarboxylic anhydride (5.00 g, 33.3 mmol), hydrazine hydrate (2.8 g, 56 mmol), and acetic acid (40.4 ml, 33.3 mmol) were mixed at RT. White precipitated crashed out. The reaction was heated under reflux for approximately 20 min. The reaction was cooled to RT and the solids were filtered, washed with water, and dried under vacuum. The product, 6,7-dihydropyrazino[2,3-d]pyridazine-5,8-dione was obtained as white solid. 1H NMR (Bruker, 400 MHz, D2O) ppm: 8.87 (s, 2H).

Workup

  1. customThe title compound was prepared
  2. customWhite precipitated
  3. temperatureThe reaction was heated
  4. temperatureunder reflux for approximately 20 min
  5. filtrationthe solids were filtered
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-2fc91df96b494e9cb0b925390975d41c
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Linked notes

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