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

HRID 325314

Reaction equation

HRID 325314 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-65fc62c2f18c4b18b88b598b140daa3d
Source dataset
uspto-grants-1984_04
Patent number
US04440785

Linked notes

Loading…