HCID 88827883, compound → HCID 88828066, compound

HRID 2399135Notes

Reaction equation

HRID 2399135 reaction equation
[Na+:1].[Na+].[N+:3]([C:6]1[CH:32]=[CH:31][C:9]([C:10]([NH:12][C:13]2[C:22]3[C:21]([S:23]([O-:26])(=[O:25])=[O:24])=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]([S:27]([O-:30])(=[O:29])=[O:28])=[CH:15][CH:14]=2)=[O:11])=[CH:8][CH:7]=1)([O-])=O.[H][H]>[Pd].O>[Na+:1].[Na+:1].[NH2:3][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:12][C:13]2[C:22]3[C:21]([S:23]([O-:26])(=[O:25])=[O:24])=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]([S:27]([O-:30])(=[O:29])=[O:28])=[CH:15][CH:14]=2)=[O:11])=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 88827883HCID 88827883, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 88828066HCID 88828066, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 10.0 g of 4-p-nitrobenzamido-1,5-naphthalenedisulfonic acid disodium salt (prepared as in Example 3), 200 ml of water and 1.0 g of 10% palladium on charcoal is hydrogenated in a Parr shaker for 11/2 hours at room temperature with an initial pressure of 46 pounds of hydrogen. During this time a total of 4.5 pounds of hydrogen is absorbed. The mixture is heated to dissolve some precipitated product and is filtered hot to remove the catalyst. The filtrate is then evaporated to a small volume in vacuo at about 60° C. and a copious amount of absolute ethyl alcohol is added. The product is collected by filtration and is washed with absolute ethyl alcohol followed by ether. After air drying the material is oven dried at 120° C. overnight.

Workup

  1. custom2 hours
  2. customat room temperature
  3. customDuring this time a total of 4.5 pounds of hydrogen is absorbed
  4. temperatureThe mixture is heated
  5. dissolutionto dissolve some precipitated product
  6. filtrationis filtered hot
  7. customto remove the catalyst
  8. customThe filtrate is then evaporated to a small volume in vacuo at about 60° C.
  9. additiona copious amount of absolute ethyl alcohol is added
  10. filtrationThe product is collected by filtration
  11. washis washed with absolute ethyl alcohol
  12. customAfter air drying the material
  13. customdried at 120° C. overnight

Sources & evidence

ORD record
ord-c8cfe5599cec4506a582ab3c35876121
Source dataset
uspto-grants-1977_05
Patent number
US04027038

Reaction notes

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