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

HRID 911115Notes

Reaction equation

HRID 911115 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-e5fc0b40d2964d6989d13794855ad682
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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