Acetic Anhydride → 3-Acetamidopyrazine-2-carboxylic acid o-toluamide

HRID 1737259Notes

Reaction equation

HRID 1737259 reaction equation
[C:1]1([CH3:10])[C:2]([C:7]([NH2:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:11][C:12]1[C:13]([C:18]([OH:20])=[O:19])=[N:14][CH:15]=[CH:16][N:17]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:1]1([CH3:10])[C:2]([C:7]([NH2:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:21]([NH:11][C:12]1[C:13]([C:18]([OH:20])=[O:19])=[N:14][CH:15]=[CH:16][N:17]=1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 697096873-Aminopyrazine-2carboxylic acid o-toluamide

Product 1

HCID 697097723-Acetamidopyrazine-2-carboxylic acid o-toluamideYield 76%

Procedure

A mixture of 3-aminopyrazine-2-carboxylic acid o-toluamide (1.0 g, 4.39 mmol) and acetic anhydride (12 mL) was refluxed 2 hours. The solvent was removed and the residue was triturated with hot ethyl acetate. The ethyl acetate slurry was cooled and the product was collected and rinsed with ether to afford 0.893 g (76%) of 3-acetamidopyrazine-2-carboxylic acid o-toluamide.

Workup

  1. temperaturewas refluxed 2 hours
  2. customThe solvent was removed
  3. customthe residue was triturated with hot ethyl acetate
  4. temperatureThe ethyl acetate slurry was cooled
  5. customthe product was collected
  6. washrinsed with ether

Sources & evidence

ORD record
ord-09d87626a78e48dbae57f4faed0fa2c0
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

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