Trifluoroacetic acid → 5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one

HRID 2352778

Reaktionsgleichung

Reaktionsgleichung von HRID 2352778
FC(F)(F)C(O)=O.[BH4-].[Na+].[N+:10]([C:13]1[CH:30]=[CH:29][C:16]([C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22]3)=O)=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([CH2:17][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22]3)=[CH:29][CH:30]=1)([O-:12])=[O:11]

Komponenten

4

Edukt 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 687007145-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one

Produkt 1

HCID 687018775-(4-Nitro-benzyl)-1,3-dihydro-indol-2-oneAusbeute 61 %

Versuchsvorschrift

In a dried 250 mL round bottom flask, 20.73 mL of trifluoroacetic acid was added and then cooled to 0° C. under Ar(g). NaBH4 in pellet form (1.35 g, 35.71 mmol, ˜1.5 pellets) was added to the flask. 5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 7, 1.0 g, 3.55 mmol) was then added in slowly over 15 min. After the addition was completed, the reaction was allowed to warm to room temperature and was stirred for 36 hours forming a yellow foamy mixture. The mixture was poured over ice-water and allowed to warm to room temperature, during which a tan solid precipitated out of solution. The tan solid was collected by filtration and washed with water affording 5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one in 61% yield (0.589 g, 2.165 mmol).

Aufarbeitung

  1. additionAfter the addition
  2. customforming a yellow foamy mixture
  3. temperatureto warm to room temperature, during which a tan solid
  4. customprecipitated out of solution
  5. filtrationThe tan solid was collected by filtration
  6. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-5a27ecb47f3b4eb783370ed8f2280656
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749530B2

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