Acetamide → N-Acetyl-5-nitropyridine-3-carboxamide

HRID 972756Notes

Reaction equation

HRID 972756 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].[H-].[Na+].[N+:7]([C:10]1[CH:11]=[N:12][CH:13]=[C:14]([CH:18]=1)[C:15](Cl)=[O:16])([O-:9])=[O:8]>CN(C)C=O>[C:1]([NH:4][C:15](=[O:16])[C:14]1[CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=[N:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 178AcetamideHCID 24758Sodium hydrideHCID 214053565-Nitro-3-pyridinecarbonyl chloride

Product 1

HCID 21405283N-Acetyl-5-nitropyridine-3-carboxamideYield 6.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dimethylformamide was dissolved 0.29 g of acetamide, and to this solution was added 0.24 g of NaH (mineral oil 50%). The mixture was then stirred at room temperature for 2 hours. To the mixture was added 0.93 g of 5-nitronicotinic acid chloride, and this was stirred overnight at room temperature. The solvent was evaporated under reduced pressure. The obtained residue was, after addition of water, extracted with ethyl acetate. The extract was dried over sodium sulfate and evaporated to remove the solvent. The obtained product was purified on a silica gel column and recrystallized from ethyl acetate - petroleum ether to give 0.07 g of the desired compound melting at 162° - 163° C.

Workup

  1. stirringthis was stirred overnight at room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. additionafter addition of water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over sodium sulfate
  6. customevaporated
  7. customto remove the solvent
  8. customThe obtained product was purified on a silica gel column
  9. customrecrystallized from ethyl acetate - petroleum ether

Sources & evidence

ORD record
ord-ae0de909014c4e499ac07a9b8371cecf
Source dataset
uspto-grants-1977_10
Patent number
US04053608

Reaction notes

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