HCID 88828681, compound → 4-(m-Aminobenzamido)-1,5-naphthalenedisulfonic acid disodium salt

HRID 2399137Notes

Reaction equation

HRID 2399137 reaction equation
[Na+:1].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][CH:32]=1)[C:9]([NH:11][C:12]1[C:21]2[C:20]([S:22]([O-:25])(=[O:24])=[O:23])=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]([S:26]([O-:29])(=[O:28])=[O:27])=[CH:14][CH:13]=1)=[O:10])([O-])=O.[H][H]>[Pd].O>[Na+:1].[Na+:1].[NH2:3][C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][CH:32]=1)[C:9]([NH:11][C:12]1[C:21]2[C:20]([S:22]([O-:25])(=[O:24])=[O:23])=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]([S:26]([O-:29])(=[O:28])=[O:27])=[CH:14][CH:13]=1)=[O:10]

Participants

5

Reactant 2

HCID 88828681HCID 88828681, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 888279644-(m-Aminobenzamido)-1,5-naphthalenedisulfonic acid disodium salt

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 25.0 g of 4-(m-nitrobenzamido)-1,5-naphthalenedisulfonic acid disodium salt (prepared as in Example 5), 200 ml of water and 2.0 g of 10% palladium on charcoal is hydrogenated in a Parr shaker for 4 hours and 20 minutes at room temperature with an initial pressure of 42 pounds of hydrogen. During this time a total of 11.0 pounds of hydrogen is absorbed. The mixture is heated to dissolve some precipitated product and is filtered through diatomaceous earth to remove the catalyst. The filtrate is then evaporated to a small volume in vacuo at 55°-60° C. until crystal formation. The material is then diluted with absolute ethyl alcohol and is triturated. The crystals are then collected by filtration and the product is washed first with two 100 ml portions of absolute ethyl alcohol followed by two 100 ml portions of ether. The product of the example is then oven dried overnight at 120° C.

Workup

  1. customDuring this time a total of 11.0 pounds of hydrogen is absorbed
  2. temperatureThe mixture is heated
  3. dissolutionto dissolve some precipitated product
  4. filtrationis filtered through diatomaceous earth
  5. customto remove the catalyst
  6. customThe filtrate is then evaporated to a small volume in vacuo at 55°-60° C. until crystal formation
  7. additionThe material is then diluted with absolute ethyl alcohol
  8. customis triturated
  9. filtrationThe crystals are then collected by filtration
  10. washthe product is washed first with two 100 ml portions of absolute ethyl alcohol
  11. customoven dried overnight at 120° C.

Sources & evidence

ORD record
ord-066d73203bdb4f6682d6d077f20cc2a6
Source dataset
uspto-grants-1977_05
Patent number
US04027038

Reaction notes

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