Acetamide → 3,4-Pyridinedicarboximide

HRID 1784374Notes

Reaction equation

HRID 1784374 reaction equation
[CH:1]1[C:6]([C:7](O)=[O:8])=[C:5]([C:10]([OH:12])=O)[CH:4]=[N:3][CH:2]=1.C(OC(=O)C)(=O)C.C([NH2:23])(=O)C>>[C:7]1(=[O:8])[C:6]2[CH:1]=[CH:2][N:3]=[CH:4][C:5]=2[C:10](=[O:12])[NH:23]1

Participants

4

Reactant 3

HCID 178AcetamideHCID 7918Acetic AnhydrideHCID 10273Cinchomeronic acid

Product 1

HCID 729263,4-PyridinedicarboximideYield 95.1%

Conditions

Temperature
145 °C

Procedure

A suspension of cinchomeronic acid (30)(50 g, 300 mmol) in acetic anhydride (123.5 g, 1200 mmol) was heated to reflux (140-150° C.) until all solid material dissolved and the mixture was homogeneous. The mixture was then cooled and concentrated in vacuo. Acetamide (50 g, 846 mmol) was then added and the mixture heated to 140° C. for 3 hours whereupon it was then cooled to room temperature. The solid residue that formed upon cooling was pulverized and triturated with water (100 ml), filtered and washed with more water and dried in a desiccator to give the title compound (42.26 g, 95.1%) in suitably pure form to be used without any further purification. m/z (LC-MS, ESP): 149 [M+H]+, R/T=0.44 mins.

Workup

  1. temperaturewas heated
  2. dissolutiondissolved
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated in vacuo
  5. temperaturethe mixture heated to 140° C. for 3 hours whereupon it
  6. temperaturewas then cooled to room temperature
  7. customThe solid residue that formed
  8. temperatureupon cooling
  9. customtriturated with water (100 ml)
  10. filtrationfiltered
  11. washwashed with more water
  12. customdried in a desiccator

Sources & evidence

ORD record
ord-52fe52bb7b304fe7970cc8b40a43952c
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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