Pyromellitic dianhydride → Quinoline Yellow

HRID 1607655Notes

Reaction equation

HRID 1607655 reaction equation
[CH:1]1[C:6]2C(OC(=O)[C:5]=2[CH:4]=[C:3]2[C:12]([O:14][C:15](=[O:16])[C:2]=12)=O)=O.O[C:18]1[C:19]([CH3:31])=[N:20][C:21]2[C:26]([C:27]=1C(O)=O)=[CH:25][CH:24]=[CH:23][CH:22]=2.[N+](C1C=CC=CC=1)([O-])=O>>[CH:24]1[CH:25]=[C:26]2[CH:27]=[CH:18][C:19]([CH:31]3[C:15](=[O:16])[C:2]4[C:3](=[CH:4][CH:5]=[CH:6][CH:1]=4)[C:12]3=[O:14])=[N:20][C:21]2=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 6966Pyromellitic dianhydrideHCID 7416NitrobenzeneHCID 670244-Quinolinecarboxylic acid, 3-hydroxy-2-methyl-

Product 1

HCID 6731Quinoline Yellow

Procedure

65.4 Parts of pyromellitic acid dianhydride and 61 parts of 3-hydroxy-2-methyl-quinoline-4-carboxylic acid are heated under reflux at 205° in 1000 parts of nitrobenzene for 1 hour, distilling off the water produced by the reaction. The mixture is held at this temperature for 31/2 hours. The mixture is then cooled to 10° and after stirring at this temperature for 1 hour, is filtered and the product is washed in toluene and ethanol. 93 parts of a dark brown quinophthalone intermediate result.

Workup

  1. distillationdistilling off the water
  2. customproduced by the reaction
  3. custom2 hours
  4. temperatureThe mixture is then cooled to 10°
  5. filtrationis filtered
  6. washthe product is washed in toluene

Sources & evidence

ORD record
ord-069f6e35a34d4396997f32640d2aba8f
Source dataset
uspto-grants-1989_09
Patent number
US04866113

Reaction notes

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