Oxalic Acid → Pyrido(2,3-b)pyrazine-2,3-diol

HRID 655622Notes

Reaction equation

HRID 655622 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](O)(=[O:13])[C:10](O)=[O:11]>Cl>[NH:8]1[C:10](=[O:11])[C:9](=[O:13])[NH:1][C:2]2[N:3]=[CH:4][CH:5]=[CH:6][C:7]1=2

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 99562,3-Diaminopyridine

Product 1

HCID 74947Pyrido(2,3-b)pyrazine-2,3-diolYield 90.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 2,3-diaminopyridine (20 g, 0.136 mol) in 4N aqueous HCl (200 ml) is added oxalic acid (20.7 g, 0.164 mol) and the reaction mixture is refluxed for 20 h. The reaction mixture is cooled and the solid precipitated is filtered, washed with water and dried under vacuum to afford 20 g (89%) of the title compound as a solid. HPLC (max plot) 98%.

Workup

  1. temperaturethe reaction mixture is refluxed for 20 h
  2. temperatureThe reaction mixture is cooled
  3. customthe solid precipitated
  4. filtrationis filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-44595e1950244a75944f176da37f0f04
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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