1-Methyl-7-benzoylindoline → 1-Methyl-7-benzoylindole

HRID 27361Notes

Reaction equation

HRID 27361 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:4]=[CH:3]1

Participants

4

Reactant 1

HCID 233426791-Methyl-7-benzoylindoline

Product 1

HCID 201894801-Methyl-7-benzoylindoleYield 85%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.4 grams (0.01 mole) of 1-methyl-7-benzoylindoline and 8.7 grams (0.1 mol) of manganese dioxide in 25 ml of methylene chloride was heated at reflux for 18 hours. The mixture was cooled and filtered. The filtrate was concentrated and the resulting residue was distilled to give 2 grams of 1-methyl-7-benzoylindole having a b.p. of 128° C./0.03 mm Hg.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. distillationthe resulting residue was distilled

Sources & evidence

ORD record
ord-90919a21f3e44b4aa4b27f128eb16600
Source dataset
uspto-grants-1980_09
Patent number
US04221716

Reaction notes

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