Tartrazine → 8-(5-Amino-o-toluenesulfonamido)-1,3,6-naphthalenetrisulfonic acid

HRID 263061Notes

Reaction equation

HRID 263061 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([S:11]([NH:14][C:15]2[CH:16]=[C:17]([S:33]([OH:36])(=[O:35])=[O:34])[CH:18]=[C:19]3[C:24]=2[C:23]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:22][C:21]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:20]3)(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O.C1C(N=NC2C(=O)N(C3C=CC(S([O-])(=O)=O)=CC=3)N=C2C([O-])=O)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+].[Na+]>[Pd].O>[NH2:1][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([S:11]([NH:14][C:15]2[CH:16]=[C:17]([S:33]([OH:36])(=[O:35])=[O:34])[CH:18]=[C:19]3[C:24]=2[C:23]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:22][C:21]([S:29]([OH:32])(=[O:30])=[O:31])=[CH:20]3)(=[O:13])=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 164825TartrazineHCID 867365448-(5-Nitro-o-toluenesulfonamido)-1,3,6-naphthalenetrisulfonic acid

Product 1

HCID 867365468-(5-Amino-o-toluenesulfonamido)-1,3,6-naphthalenetrisulfonic acidYield 79.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 20.0 g of 8-(5-nitro-o-toluenesulfonamido)-1,3,6-naphthalenetrisulfonic acid, trisodium salt, 90.0 ml of water and 20.0 g of 10% palladium on carbon catalyst is hydrogenated as described in Example 1. The reaction mixture is filtered through diatomaceous earth and the filtrate is evaporated. The residue is dissolved in a minimum amount of water, then is added dropwise to 800 ml of stirred absolute ethanol. The mixture is stirred for 2 hours and allowed to stand for 48 hours. A light yellow solid is collected, washed with ethanol and ether, then is dried to yield 15.0 g of 8-(5-amino-o-toluenesulfonamido)-1,3,6-naphthalenetrisulfonic acid, trisodium salt.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. customthe filtrate is evaporated
  3. dissolutionThe residue is dissolved in a minimum amount of water
  4. additionis added dropwise to 800 ml of stirred absolute ethanol
  5. waitto stand for 48 hours
  6. customA light yellow solid is collected
  7. washwashed with ethanol and ether
  8. customis dried

Sources & evidence

ORD record
ord-6ebbae4e313347f6895bfbb379ebd892
Source dataset
uspto-grants-1979_05
Patent number
US04155930

Reaction notes

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