Aniline → 6-Anilino-5,8-quinolinedione

HRID 2412431Notes

Reaction equation

HRID 2412431 reaction equation
[N:1]1[C:10]2[C:9](=[O:11])[CH:8]=[CH:7][C:6](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Ce+3].[Cl-].[Cl-]>C(O)C>[NH:13]([C:7]1[C:6](=[O:12])[C:5]2[CH:4]=[CH:3][CH:2]=[N:1][C:10]=2[C:9](=[O:11])[CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 24636Cerium(III) chlorideHCID 3883065,8-Dihydroquinoline-5,8-dione

Product 1

HCID 39766-Anilino-5,8-quinolinedione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Twenty and one-half grams of quinoline-5,8-quinone were dissolved in 500 ml of absolute ethanol, then 13 g of aniline were added, followed by the addition of 32 g of cerium chloride. This reaction mixture was refluxed overnight. The resulting mixture had a brown-blue color and was stirred and then left to cool to room temperature for about 26 hours.

Workup

  1. temperatureThis reaction mixture was refluxed overnight
  2. waitleft

Sources & evidence

ORD record
ord-0282439f41104f159b40942a981c5397
Source dataset
uspto-grants-1985_01
Patent number
US04492704

Reaction notes

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