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

HRID 1828540

Reaction equation

HRID 1828540 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]>O>[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

4

Reactant 2

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

Product 1

HCID 13567013N-(4-methyl-5-nitropyridin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

4-Methyl-5-nitro-2-pyridinamine (3.69 g, 2.41 mmol) was added with acetic anhydride (10 ml) and stirred at 130° C. for 1.5 hours. The reaction mixture was left stand for cooling, and then added with distilled water (5.4 ml) at 0° C., heated to 130° C., and stirred for 45 minutes. The reaction mixture was left stand for cooling and concentrated, and the deposited crystals were collected by filtration and washed with distilled water to obtain the title compound (4.71 g, quantitative).

Workup

  1. waitThe reaction mixture was left stand
  2. temperaturefor cooling
  3. temperatureheated to 130° C.
  4. stirringstirred for 45 minutes
  5. waitThe reaction mixture was left stand
  6. temperaturefor cooling
  7. concentrationconcentrated
  8. filtrationthe deposited crystals were collected by filtration
  9. washwashed with distilled water

Sources & evidence

ORD record
ord-ae1dc800dc2640f1a468cc2b45daad5f
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Linked notes

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