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

HRID 579969

Reaction equation

HRID 579969 reaction equation
[C:1]([NH:4][C:5]1[C:6]([CH3:12])=[CH:7][CH:8]=[CH:9][C:10]=1[CH3:11])(=[O:3])[CH3:2].C(O)(=O)C.S(=O)(=O)(O)O.[N+:22]([O-])([OH:24])=[O:23]>>[C:1]([NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([N+:22]([O-:24])=[O:23])[C:6]=1[CH3:12])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 16616N-Acetyl-2,6-xylidine

Product 1

HCID 223591N-(2,6-dimethyl-3-nitrophenyl)acetamideYield 94.7%

Procedure

To a mixture of 30.1 g of N-acetyl-2,6-xylidine (0.18 mole) and 40 ml of acetic acid (0.70 mole) was added gradually 80 ml of concentrated sulfuric acid (0.50 mole) with stirring under ice-cooling. Then, to the mixture was added slowly 10 ml of fuming nitric acid (0.24 mole) in a manner such that the temperature of the reaction mixture did not exceed 10° C. The reaction mixture was returned to room temperature and, after stirring for 2 hours, poured onto ice. The resulting crystalline precipitate was collected by filtration and recrystallized from ethanol to give 35.5 g (92%) of the title compound (m.p. 171°-173° C.; pale yellow needles).

Workup

  1. temperaturecooling
  2. customdid not exceed 10° C
  3. customwas returned to room temperature
  4. stirringafter stirring for 2 hours
  5. additionpoured onto ice
  6. filtrationThe resulting crystalline precipitate was collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9cf9010d1b0847ef8edf5c898db9a212
Source dataset
uspto-grants-1988_06
Patent number
US04751232

Linked notes

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