Acetic Anhydride → N-(4-methyl-5-nitropyridin-2-yl)acetamide

HRID 2201774Notes

Reaction equation

HRID 2201774 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([NH2:11])[CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 2431652-Amino-4-methyl-5-nitropyridine

Product 1

HCID 13567013N-(4-methyl-5-nitropyridin-2-yl)acetamideYield 87%

Conditions

Temperature
90 °C

Procedure

A mixture of 4-methyl-5-nitropyridin-2-amine (5 g, 32 mmol) and acetic anhydride (20 mL) was heated at 90° C. for 4 hours. After cooling the solvent was evaporated under vacuum. The concentrated mass was dissolved in toluene and evaporated under vacuum. The resulting solid was triturated with diethyl ether and filtered to afford N-(4-methyl-5-nitropyridin-2-yl)acetamide (5.5 g, 87%).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas evaporated under vacuum
  3. dissolutionThe concentrated mass was dissolved in toluene
  4. customevaporated under vacuum
  5. customThe resulting solid was triturated with diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-252a2c3610bf42a4a52472a7b9e5b9e5
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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