1-(2,3-Dihydro-1H-indol-7-yl)ethan-1-one → 1-(1H-indol-7-yl)ethanone

HRID 4476

Reaction equation

HRID 4476 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH2:10][CH2:9]2)(=[O:3])[CH3:2]>[O-2].[O-2].[Mn+4].C(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 136994211-(2,3-Dihydro-1H-indol-7-yl)ethan-1-one

Product 1

HCID 137705341-(1H-indol-7-yl)ethanoneYield 76%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst3×HCID 6344DichloromethaneSolvent

Procedure

To 30 g. (0.186 mole) of 7-acetylindoline in 415 ml. of methylene chloride was added 48.5 g (0.56 mole) of manganese dioxide and the mixture refluxed through a soxhlet filled with 4A molecular sieves for 22 hours. The mixture was cooled and an additional 48.5 g. of manganese dioxide was added. Fresh molecular sieves were added and the refluxing continued for 5 hours. The same amount of manganese dioxide and molecular sieves were added again and the refluxing was continued for one hour. The mixture was filtered and the filtrate concentrated to dryness. The residue was triturated with hexane and filtered, 22.57 g. (76% yield), m.p. 65°-66° C.

Workup

  1. temperaturethe mixture refluxed through a soxhlet
  2. temperatureThe mixture was cooled
  3. additionFresh molecular sieves were added
  4. waitthe refluxing was continued for one hour
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated to dryness
  7. customThe residue was triturated with hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-72e6c5070b794368854183d6caa959fa
Source dataset
uspto-grants-1988_02
Patent number
US04725616

Linked notes

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