4-Benzoyl-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one → 4-Benzoyl-1,3-dihydro-2H-indol-2-one

HRID 2051870Notes

Reaction equation

HRID 2051870 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11](SC)[C:12](=[O:18])[NH:13]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].O1CCCC1>[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12](=[O:18])[NH:13]2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 129235524-Benzoyl-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 129012464-Benzoyl-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of 7.0 g. (0.0248 mole) of 4-benzoyl-3-methylthioindolin-2-one in 400 ml. of tetrahydrofuran was treated portionwise under a nitrogen atmosphere with 35.0 g. of Raney nickel over a 2.5 hr. period. The reaction mixture was stirred for 1.5 hr. after addition as complete and the catalyst removed by filtration. The filter cake was washed well with tetrahydrofuran and methylene chloride and the filtrate evaporated under reduced pressure. The residue (5.6 g.) was recrystallized from methanol and gave 4.45 g. (76%) of product m.p. 210°-212° C.

Workup

  1. additionA stirred suspension of 7.0 g
  2. additionafter addition as complete and the catalyst
  3. customremoved by filtration
  4. washThe filter cake was washed well with tetrahydrofuran and methylene chloride
  5. customthe filtrate evaporated under reduced pressure
  6. customThe residue (5.6 g.) was recrystallized from methanol
  7. customgave 4.45 g

Sources & evidence

ORD record
ord-8f29148ff5eb4c049af611e61c24d96b
Source dataset
uspto-grants-1980_01
Patent number
US04182774

Reaction notes

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