Water → HCID 131711175, compound

HRID 867137Notes

Reaction equation

HRID 867137 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([O-])=O.[OH-:16].[Na+:17].[OH2:18]>[Pd]>[Na+:17].[Na+:17].[Na+:17].[Na+:17].[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([NH:1][C:4]2[CH:12]=[C:8]([C:9]([O-:11])=[O:10])[CH:7]=[C:6]([CH:5]=2)[C:13]([O-:15])=[O:14])=[O:14])[CH:7]=[C:8]([C:9]([NH:1][C:4]2[CH:5]=[C:6]([C:13]([O-:15])=[O:14])[CH:7]=[C:8]([CH:12]=2)[C:9]([O-:11])=[O:10])=[O:10])[CH:12]=1)([O-:18])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 120695-Nitroisophthalic acidHCID 14798Sodium Hydroxide

Product 1

HCID 131711175HCID 131711175, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 21.1 g of 5-nitroisophthalic acid, 40.5 ml of 5N sodium hydroxide and 2.0 g of 10% palladium on carbon catalyst in 110 ml of water is hydrogenated at room temperature for 1 hour and then filtered through diatomaceous earth. To the solution of 5-aminoisophthalic acid disodium salt is added 9.2 g of sodium bicarbonate followed by 13.65 g of powdered 5-nitroisophthaloyl chloride (prepared as described in Example 1). The solution is cooled in a water bath and stirred vigorously in a baffle flask for 1 hour and 15 minutes. The mixture is filtered, the filtrate is concentrated to approximately 125 ml and 200 ml of ethanol is added to give a yellow precipitate. The mixture is filtered and the product is washed with 66% aqueous ethanol, ethanol and ether. The material is dried, then dissolved in 200 ml of water. The solution is filtered through diatomaceous earth and diluted slowly with stirring and warming with 300 ml of ethanol. The precipitate formed is collected and washed with 100 ml of 60% aqueous ethanol, 400 ml of ethanol and ether. The product is dried by conventional means to give 27.8 g of 5,5'-[5-nitro-1,3-phenylenebis(carbonylimino)]diisophthalic acid tetrasodium salt.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. additionTo the solution of 5-aminoisophthalic acid disodium salt is added 9.2 g of sodium bicarbonate
  3. temperatureThe solution is cooled in a water bath
  4. filtrationThe mixture is filtered
  5. concentrationthe filtrate is concentrated to approximately 125 ml and 200 ml of ethanol
  6. additionis added
  7. customto give a yellow precipitate
  8. filtrationThe mixture is filtered
  9. washthe product is washed with 66% aqueous ethanol, ethanol and ether
  10. customThe material is dried
  11. dissolutiondissolved in 200 ml of water
  12. filtrationThe solution is filtered through diatomaceous earth
  13. additiondiluted slowly
  14. stirringwith stirring
  15. temperaturewarming with 300 ml of ethanol
  16. customThe precipitate formed
  17. customis collected
  18. washwashed with 100 ml of 60% aqueous ethanol, 400 ml of ethanol and ether
  19. customThe product is dried by conventional means

Sources & evidence

ORD record
ord-02ea6313263b46e3ac4be8d0789c4807
Source dataset
uspto-grants-1978_07
Patent number
US04102917

Reaction notes

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