3-Methylthio-5-phenylindolin-2-one → 5-Phenyloxindole

HRID 652257

Reaktionsgleichung

Reaktionsgleichung von HRID 652257
CS[CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=2)[NH:5][C:4]1=[O:18]>[Ni].O.O1CCCC1>[C:12]1([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][C:4](=[O:18])[CH2:3]3)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

4

Edukt 1

HCID 133019763-Methylthio-5-phenylindolin-2-one

Produkt 1

HCID 133019785-Phenyloxindole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 444642Hydroxy-nickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a slurry of 11.2 g. (0.044 mole) of 3-methylthio-5-phenylindolin-2-one in 500 ml. of tetrahydrofuran was added 100 g. of a commercial Raney nickel/water preparation portionwise over a 2 hr. period. The mixture was filtered through celite and the filtrate was concentrated. A small amount of methylene chloride was added to the residue and the resulting solid was collected by filtration. This solid was recrystallized from toluene to give 6.2 g. (67%) of product as a tan solid, m.p. 214°-15° C.

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. additionA small amount of methylene chloride was added to the residue
  4. filtrationthe resulting solid was collected by filtration
  5. customThis solid was recrystallized from toluene
  6. customto give 6.2 g

Quellen und Nachweise

ORD-Eintrag
ord-9f2968ea953f463190be3ab138780771
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670566

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