Nitric Acid → N-(2,6-dimethyl-4-nitrophenyl)acetamide

HRID 1820115Notes

Reaction equation

HRID 1820115 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[C:10]([O:13]C(=O)C)(=O)[CH3:11].[N+:17]([O-])([OH:19])=[O:18]>C(O)(=O)C>[CH3:1][C:2]1[CH:8]=[C:7]([N+:17]([O-:19])=[O:18])[CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:10](=[O:13])[CH3:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 68962,6-DimethylanilineHCID 7918Acetic Anhydride

Product 1

HCID 50851089N-(2,6-dimethyl-4-nitrophenyl)acetamideYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

2,6-Dimethylaniline (30.2 g) was added slowly to acetic anhydride (200 mL) cooled to 0° C. over 10 minutes. After 30 minutes, acetic acid (40 mL) and fuming nitric acid (15 mL) were added to the reaction mixture and the cooling was removed. The reaction mixture was filtered after 1 hour and the crystals were washed with water and dried in vacuo to furnish 5.20 g (30% yield) of the title compound as a yellow solid. 1H NMR (500 MHz, DMSO-d6): 2.10 (s, 3H), 2.26 (s, 6H), 7.98 (s, 2H), 9.61 (s, 1H).

Workup

  1. customthe cooling was removed
  2. filtrationThe reaction mixture was filtered after 1 hour
  3. washthe crystals were washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8a72de630b20452bafd5f643f8471047
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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