Aniline → 6-Anilino-5,8-quinolinedione

HRID 2412430Notes

Reaction equation

HRID 2412430 reaction equation
CO[C:3]1[C:4](=[O:14])[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:10]=2[C:11](=[O:13])[CH:12]=1.[Cl-].[Ce+3].[Cl-].[Cl-].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[NH:19]([C:3]1[C:4](=[O:14])[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:10]=2[C:11](=[O:13])[CH:12]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 24636Cerium(III) chlorideHCID 2536866-methoxyquinoline-5,8-dione

Product 1

HCID 39766-Anilino-5,8-quinolinedioneYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Six grams of 6-methoxyquinoline-5,8-quinone were dissolved in 500 ml of absolute ethanol and 9 g of cerium chloride were added. After the reaction was stirred, 3.3 g of aniline were added. The reaction mixture was refluxed for several hours, then it was stirred overnight at room temperature. The ethanol was evaporated to dryness and partitioned between chloroform and an aqueous sodium chloride solution. The chloroform layer was washed with an aqueous sodium chloride solution, dried with sodium sulfate, and then evaporated. The product was crystallized from absolute ethanol and weighed 3 g (16% yield). It had a melting point of about 182°-184° and the mass spectrum indicated the expected molecular ion at m/e=250.

Workup

  1. temperatureThe reaction mixture was refluxed for several hours
  2. stirringit was stirred overnight at room temperature
  3. customThe ethanol was evaporated to dryness
  4. custompartitioned between chloroform
  5. washThe chloroform layer was washed with an aqueous sodium chloride solution
  6. dry with materialdried with sodium sulfate
  7. customevaporated
  8. customThe product was crystallized from absolute ethanol

Sources & evidence

ORD record
ord-023ff8e2d9104fb4ace9374d5e4bc2e6
Source dataset
uspto-grants-1985_01
Patent number
US04492704

Reaction notes

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