2-Hydrazinopyridine → 4-Hydroxy-3-[2-(2-pyridinyl)diazenyl]-1-naphthalenesulfonic acid

HRID 1395624Notes

Reaction equation

HRID 1395624 reaction equation
[Na+].[C:2]1(=[O:17])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([O-:15])(=[O:14])=[O:13])=[CH:4][C:3]1=O.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][NH2:25]>O.Cl>[OH:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:4][C:3]=1[N:25]=[N:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1

Participants

5

Reactant 2

HCID 786452-HydrazinopyridineHCID 516996Sodium beta-naphthoquinone-4-sulfonate

Product 1

HCID 827254-Hydroxy-3-[2-(2-pyridinyl)diazenyl]-1-naphthalenesulfonic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

1,2-Naphthoquinone-4-sulfonic acid sodium salt (26 g) was dissolved in a mixture of water (500 ml) and concentrated hydrochloric acid (250 ml). To this solution was added 2-pyridylhydrazine (11 g) in water (100 ml). The reaction mixture became warm and the product started to precipitate. After 30 minutes of cooling, the product was filtered off and washed with a small volume of water, acetone and ether. Yield 32 g (96 percent).

Workup

  1. temperatureThe reaction mixture became warm
  2. customto precipitate
  3. temperatureAfter 30 minutes of cooling
  4. filtrationthe product was filtered off
  5. washwashed with a small volume of water, acetone and ether

Sources & evidence

ORD record
ord-a4a29f3b324e46f8b140a483403a9673
Source dataset
uspto-grants-1980_05
Patent number
US04204870

Reaction notes

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