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

HRID 652257

Reaction equation

HRID 652257 reaction equation
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

Participants

4

Reactant 1

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

Product 1

HCID 133019785-Phenyloxindole

Reagents, catalysts & solvents 2

HCID 444642Hydroxy-nickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9f2968ea953f463190be3ab138780771
Source dataset
uspto-grants-1987_06
Patent number
US04670566

Linked notes

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