3-Methylthio-7-phenylindolin-2-one → 7-phenyl-2,3-dihydro-1H-indol-2-one

HRID 652259

Reaction equation

HRID 652259 reaction equation
CS[CH:3]1[C:11]2[C:6](=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:18]>[Ni].O.O1CCCC1>[C:12]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=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 133019753-Methylthio-7-phenylindolin-2-one

Product 1

HCID 133019777-phenyl-2,3-dihydro-1H-indol-2-one

Reagents, catalysts & solvents 2

HCID 444642Hydroxy-nickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 21.5 g. (0.084 mole) of 3-methylthio-7-phenylindolin-2-one in 400 ml. of tetrahydrofuran was treated portionwise with 110 g. of a commercial Raney nickel/water slurry over a 3 hr. period. The mixture was filtered through Celite and the filtrate was concentrated to a gummy residue. The residue was recrystallized from cyclohexane-benzene to yield 7.6 g. (43%) of product as tan needles, m.p. 167°-169° C.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated to a gummy residue
  3. customThe residue was recrystallized from cyclohexane-benzene
  4. customto yield 7.6 g

Sources & evidence

ORD record
ord-ee1ec1c35bbb4f9287d842e8765a94ea
Source dataset
uspto-grants-1987_06
Patent number
US04670566

Linked notes

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