Nitric Acid → N-(2,6-dimethyl-3-nitrophenyl)acetamide

HRID 1771632Notes

Reaction equation

HRID 1771632 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:12])[CH3:11].[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O.C(O)(=O)C>[CH3:8][C:4]1[C:5]([N+:13]([O-:15])=[O:14])=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10](=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 16616N-Acetyl-2,6-xylidine

Product 1

HCID 223591N-(2,6-dimethyl-3-nitrophenyl)acetamideYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

N-(2,6-dimethylphenyl)acetamide (10 g, 60 mmol, 1.0 eq) was dissolved in a mixture of H2SO4 (40 mL) and acetic acid (20 mL) at 0° C. A mixture of HNO3 (10 mL) and H2SO4 (8 mL) was added dropwise with stirring. The reaction was allowed to warm to room temperature and stirred for a further 1 h. The reaction was quenched by pouring into ice water, and the solid that formed collected by filtration to give the title compound as a yellow solid (12 g, 94%).

Workup

  1. additionwas added dropwise
  2. stirringstirred for a further 1 h
  3. customThe reaction was quenched
  4. additionby pouring into ice water
  5. customthe solid that formed
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-fe6f7a514b84428db5384ca2a0996faa
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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