Acetic Acid → N-(5-Nitro-1,3-dioxo-1,3-dihydroisobenzofuran-4-yl)acetamide

HRID 992491노트

반응식

HRID 992491 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

HCID 15511835N-(5-Nitro-1,3-dioxo-1,3-dihydroisobenzofuran-4-yl)acetamide

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5de86976a84143a5aaa16afadef8343d
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469051B2

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