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

HRID 875381

Reaction equation

HRID 875381 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-d06bd54f5f924e2ebe9150a2b1d7623e
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Linked notes

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