7-(4-Chlorobenzoyl)-3-methylthioindolin-2-one → 7-(4-Chlorobenzoyl)-1,3-dihydro-2H-indol-2-one

HRID 442542Notes

Reaction equation

HRID 442542 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:16]=2[NH:15][C:14](=[O:17])[CH:13]3SC)=[O:7])=[CH:4][CH:3]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:16]=2[NH:15][C:14](=[O:17])[CH2:13]3)=[O:7])=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 129235497-(4-Chlorobenzoyl)-3-methylthioindolin-2-one

Product 1

HCID 129235517-(4-Chlorobenzoyl)-1,3-dihydro-2H-indol-2-oneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 9 g. (0.028 mole) of 7-(4-chlorobenzoyl)-3-methylthioindolin-2-one in 180 ml. of tetrahydrofuran was treated over a two-hour period with 45 g. of a commercial Raney nickel water suspension. After the addition was complete the mixture was filtered. A drop of concentrated hydrochloric acid was added to the filtrate which removed some color and the resulting solution was then stripped under water pump vacuum to yield a cream color material. Recrystallization from toluene gave needles, (93% yield); the material sintered at 177° C. and melted at 186° C.

Workup

  1. additionAfter the addition
  2. filtrationwas filtered
  3. additionA drop of concentrated hydrochloric acid was added to the filtrate which
  4. customremoved some color
  5. customto yield a cream color material
  6. customRecrystallization from toluene
  7. customgave needles, (93% yield)
  8. customsintered at 177° C.

Sources & evidence

ORD record
ord-17565ee9daf24f67bf05fcbad50c6b75
Source dataset
uspto-grants-1977_08
Patent number
US04045576

Reaction notes

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