HCID 131711353, compound → HCID 131711351, compound

HRID 1704700Notes

Reaction equation

HRID 1704700 reaction equation
[Na+:1].[Na+].[OH:3][C:4]1[CH:13]=[C:12]([S:14]([O-:17])(=[O:16])=[O:15])[CH:11]=[C:10]2[C:5]=1[C:6]([NH:22][C:23]([C:25]1[C:26]([CH3:34])=[CH:27][C:28]([N+:31]([O-])=O)=[CH:29][CH:30]=1)=[O:24])=[CH:7][CH:8]=[C:9]2[S:18]([O-:21])(=[O:20])=[O:19]>[Pd].CN(C)C=O>[Na+:1].[Na+:1].[NH2:31][C:28]1[CH:27]=[C:26]([CH3:34])[C:25]([C:23]([NH:22][C:6]2[C:5]3[C:10](=[CH:11][C:12]([S:14]([O-:17])(=[O:16])=[O:15])=[CH:13][C:4]=3[OH:3])[C:9]([S:18]([O-:21])(=[O:20])=[O:19])=[CH:8][CH:7]=2)=[O:24])=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 131711353HCID 131711353, compound

Product 1

HCID 131711351HCID 131711351, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

An 11.0 g portion of the above nitro derivative is hydrogenated in a Parr apparatus with 1.25 g of 10% palladium on carbon and 110 ml of dimethylformamide. The reaction mixture is filtered, concentrated to a small volume and ethanol is added to a total volume of 500 ml. The mixture is concentrated to 100 ml and ether is added. The solid is collected, washed with ether and dried giving 7.8 g of 4-(5-amino-o-toluamido)-5-hydroxy-1,7-naphthalenedisulfonic acid disodium salt.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated to a small volume and ethanol
  3. additionis added to a total volume of 500 ml
  4. concentrationThe mixture is concentrated to 100 ml and ether
  5. additionis added
  6. customThe solid is collected
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-6ff2dea391ff4598a024d2975e860a2f
Source dataset
uspto-grants-1978_11
Patent number
US04127602

Reaction notes

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