8-(3-Nitro-p-toluenesulfonamido)-1,3,5-naphthalene trisulfonic acid trisodium salt → 8-(3-Amino-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acid

HRID 903846Notes

Reaction equation

HRID 903846 reaction equation
[Na+].[Na+].[Na+].[N+:4]([C:7]1[CH:8]=[C:9]([CH3:39])[CH:10]=[CH:11][C:12]=1[S:13]([NH:16][C:17]1[C:26]2[C:25]([S:27]([O-:30])(=[O:29])=[O:28])=[CH:24][C:23]([S:31]([O-:34])(=[O:33])=[O:32])=[CH:22][C:21]=2[C:20]([S:35]([O-:38])(=[O:37])=[O:36])=[CH:19][CH:18]=1)(=[O:15])=[O:14])([O-])=O.[H][H]>[Pd].O>[NH2:4][C:7]1[CH:8]=[C:9]([CH3:39])[CH:10]=[CH:11][C:12]=1[S:13]([NH:16][C:17]1[C:26]2[C:25]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:24][C:23]([S:31]([OH:34])(=[O:32])=[O:33])=[CH:22][C:21]=2[C:20]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:19][CH:18]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 1317115098-(3-Nitro-p-toluenesulfonamido)-1,3,5-naphthalene trisulfonic acid trisodium saltHCID 178418361HCID 178418361, compound

Product 1

HCID 867365488-(3-Amino-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acidYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 8.0 g of 8-(3-nitro-p-toluenesulfonamido)-1,3,5-naphthalene trisulfonic acid trisodium salt, 160 ml of water and 800 mg of 10% palladium on carbon catalyst is hydrogenated on a Parr shaker until no additional hydrogen is absorbed. The resulting mixture is filtered through diatomaceous earth and the filtrate is evaporated. The residue is dissolved in hot water and filtered. The filtrate is triturated with ethanol until cloudiness persists, then is allowed to stand at room temperature for 16 hours. The mixture is filtered and the filtrate evaporated to afford a gummy material which is dissolved in a small amount of water and triturated with ethanol. An additional 200 ml of ethanol is added and the mixture is stirred for one hour to provide a solid. The solid is collected and washed with ethanol and ether to yield 4.6 g of 8-(3-amino-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acid, trisodium salt as a light tan powder.

Workup

  1. customis absorbed
  2. filtrationThe resulting mixture is filtered through diatomaceous earth
  3. customthe filtrate is evaporated
  4. dissolutionThe residue is dissolved in hot water
  5. filtrationfiltered
  6. customThe filtrate is triturated with ethanol until cloudiness persists
  7. filtrationThe mixture is filtered
  8. customthe filtrate evaporated
  9. customto afford a gummy material which
  10. customtriturated with ethanol
  11. additionAn additional 200 ml of ethanol is added
  12. customto provide a solid
  13. customThe solid is collected
  14. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-9b9563aa9dfe4e30bbace051b569bf83
Source dataset
uspto-grants-1980_10
Patent number
US04229370

Reaction notes

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