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

HRID 992491ノート

反応式

HRID 992491 の反応式
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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5de86976a84143a5aaa16afadef8343d
出典データセット
uspto-grants-2002_10
特許番号
US06469051B2

反応ノート

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