8-Chloro-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one → 2-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

HRID 1637259Notes

Reaction equation

HRID 1637259 reaction equation
Cl[C:2]1[C:10]2[NH:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:7]3[CH2:17][CH2:18][C:19](=[O:20])[C:5]([C:6]=23)=[CH:4][CH:3]=1>[OH-].[K+].CO.[C].[Pd]>[C:11]1([C:8]2[NH:9][C:10]3[CH:2]=[CH:3][CH:4]=[C:5]4[C:19](=[O:20])[CH2:18][CH2:17][C:7]=2[C:6]=34)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 193481908-Chloro-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

Product 1

HCID 193483682-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-oneYield 39%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A portion (2.4 g) of the compound obtained in Example 60 was dissolved in a solution of potassium hydroxide (3 g) in methanol (150 ml) and to the solution was added 10% palladium-carbon (500 mg). The mixture was stirred for 30 minutes at room temperature under a hydrogen atmosphere. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10:1-2:1) to yield 700 mg (39%) of the titled compound.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10:1-2:1)

Sources & evidence

ORD record
ord-928e59bdd82b44ebaa064274670c3cd6
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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