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

HRID 442541Notes

Reaction equation

HRID 442541 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 was 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
  3. customthe catalyst removed 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-c26559bcc20b4a8d9d63e4faeba32244
Source dataset
uspto-grants-1977_08
Patent number
US04045576

Reaction notes

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