Acetic Anhydride → HCID 22172743, compound

HRID 1737269Notes

Reaction equation

HRID 1737269 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].[C:11](OC(=O)C)(=O)[CH3:12]>S(=O)(=O)(O)O>[CH3:11][C:12]1[O:9][C:8](=[O:10])[C:7]2[C:2](=[CH:3][N:4]=[CH:5][CH:6]=2)[N:1]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 4595313-Aminoisonicotinic acid

Product 1

HCID 22172743HCID 22172743, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of 3-aminopyridine-4-carboxylic acid (3.38 g, 24.5 mmol), acetic anhydride (15 mL), and sulfuric acid (3 drops) was refluxed 4 hours. The reaction was cooled and carefully quenched with solid sodium bicarbonate. The mixture was filtered through Celite® (trademark). The filtrate was extracted with ethyl acetate. This organic phase was washed with brine, dried over magnesium sulfate and concentrated to give 2-methyl-3-oxa-1,7-diaza-naphthalen-4-one (1.95 g, 49%) as a brown crystalline material.

Workup

  1. temperaturewas refluxed 4 hours
  2. temperatureThe reaction was cooled
  3. customcarefully quenched with solid sodium bicarbonate
  4. filtrationThe mixture was filtered through Celite® (trademark)
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washThis organic phase was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ee8e0e1e590849efbefb72dceee1ceb5
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

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