Ninhydrin → N-(2-(2-Hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-4,5-dimethylphenyl)acetamide

HRID 527159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527159
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH:13]1[CH:18]=[C:17]2[C:19]([C:21](O)([OH:24])[C:22](=[O:23])[C:16]2=[CH:15][CH:14]=1)=[O:20]>S(=O)(=O)(O)O>[OH:24][C:21]1([C:5]2[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=2[NH:9][C:10](=[O:12])[CH3:11])[C:22](=[O:23])[C:16]2[C:17](=[CH:18][CH:13]=[CH:14][CH:15]=2)[C:19]1=[O:20]

Komponenten

4

Edukt 2

HCID 10236NinhydrinHCID 751443',4'-Dimethylacetanilide

Produkt 1

HCID 71477898N-(2-(2-Hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-4,5-dimethylphenyl)acetamideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

N-(3,4-dimethylphenyl)acetamide (915 mg, 5.62 mmol) and ninhydrin (1.00 g, 5.62 mmol) were dissolved in conc. sulfuric acid (20 mL) and stirred at room temperature for 1.5 hrs. The reaction was stopped by slowing pouring the solution to 150 g of ice and stirring. The reaction mixture was extracted with ethylacetate and water, washed with brine. The washed organic layer was dried over sodium sulfate, concentrated in a vacuum, and purified through column chromatography (30% ethylacetate in hexane) to afford the title compound (yellow solid, 800 mg, 44%).

Aufarbeitung

  1. stirringstirring
  2. extractionThe reaction mixture was extracted with ethylacetate and water
  3. washwashed with brine
  4. dry with materialThe washed organic layer was dried over sodium sulfate
  5. concentrationconcentrated in a vacuum
  6. custompurified through column chromatography (30% ethylacetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1ee262d141c5442b91b9df91f502ade4
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346749B2

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