Acetic Acid → 3-Acetamido-4-nitrophthalic anhydride

HRID 992491Notes

Reaction equation

HRID 992491 reaction equation
CC1C(C)=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[C:13]([O:16][C:17](=[O:19])[CH3:18])(=[O:15])[CH3:14].[C:20](O)(=[O:22])[CH3:21]>>[C:20]([NH:4][C:3]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:6][CH:7]=[C:14]2[C:13]([O:16][C:17](=[O:19])[C:18]=12)=[O:15])(=[O:22])[CH3:21]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 5971662,3-Dimethyl-6-nitroaniline

Product 1

HCID 155118353-Acetamido-4-nitrophthalic anhydride

Procedure

2,3-Dimethyl-6-nitroaniline was acetylated in acetic acid by using 1 equivalence of acetic anhydride, and the product was recrystallized from ethanol. The resulting 3-acetamido-4-nitroxylene was dissolved in boiled water containing magnesium sulfate. To the solution, 6 equivalences of potassium permanganate suspended in water was added in several portions, and the solution was refluxed until purple color disappeared. The hot reaction mixture was filtered and cooled, and then the filtrate was made acidic with hydrochloric acid and extracted with ethyl acetate. The resulting 3-acetamido-4-nitrophthalic acid was dehydrated in acetic anhydride using acetyl chloride. The reaction mixture was concentrated under reduced pressure, and then a small quantity of anhydrous methylene chloride was added to the residue and the deposited solid was collected by filtration to obtain 3-acetamido-4-nitrophthalic anhydride.

Workup

  1. customthe product was recrystallized from ethanol
  2. dissolutionThe resulting 3-acetamido-4-nitroxylene was dissolved in boiled water
  3. additioncontaining magnesium sulfate
  4. additionwas added in several portions
  5. temperaturethe solution was refluxed until purple color
  6. filtrationThe hot reaction mixture was filtered
  7. temperaturecooled
  8. extractionextracted with ethyl acetate
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. additiona small quantity of anhydrous methylene chloride was added to the residue
  11. filtrationthe deposited solid was collected by filtration

Sources & evidence

ORD record
ord-5de86976a84143a5aaa16afadef8343d
Source dataset
uspto-grants-2002_10
Patent number
US06469051B2

Reaction notes

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