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

HRID 2393440Notes

Reaction equation

HRID 2393440 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[C:12]([NH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

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

Product 1

HCID 13567013N-(4-methyl-5-nitropyridin-2-yl)acetamideYield 93%

Procedure

2-Amino-4-methyl-5-nitropyridine (28.4 g, 0.185 mol) was heated at 90° C. in acetic anhydride (100 mL) for 3 hours. After cooling the solvent was evaporated in vacuo and the residue was azeotroped with toluene to give a yellow solid. This was triturated with ether and the solid was collected by filtration to give the title compound (33.8 g, 93%) as a pale yellow solid. mp 153°-154° C. 1H NMR (360 MHz, CDCl3) δ 2.27 (3H, s), 2.70 (3H, s), 8.17 (1H, br s), 8.24 (1H, s) and 8.96 (1H, s).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas evaporated in vacuo
  3. customthe residue was azeotroped with toluene
  4. customto give a yellow solid
  5. customThis was triturated with ether
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-b24bbc0bb8e847b39bfee05a0d66123d
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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