Hydrochloric Acid → 4-Hydrazino-1-naphthalenesulphonic acid hydrochloride

HRID 259899

Reaction equation

HRID 259899 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:6][CH:5]=1.[N:18]([O-])=O.[Na+].[ClH:22]>O>[ClH:22].[NH:3]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([S:14]([OH:17])(=[O:15])=[O:16])=[CH:6][CH:5]=1)[NH2:18]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 67904-Amino-1-naphthalenesulfonic acidHCID 14798Sodium Hydroxide2×HCID 23668193Sodium Nitrite

Product 1

HCID 867493604-Hydrazino-1-naphthalenesulphonic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

4 g of NaOH are added to a suspension of 22.33 g of 4-amino-1-naphthalenesulphonic acid in 125 ml of water. The mixture is cooled to 0° C. and 2 ml of concentrated NaOH are added, followed by 7.5 g of sodium nitrite and 125 g of ice to maintain the temperature at 0° C. The suspension thereby obtained is poured into 75 ml of concentrated HCl cooled beforehand to 0° C., and left stirring for 2 hours 15 minutes at this temperature. The reaction mixture is added slowly to a solution, cooled beforehand to -10° C., of 55 g of stannous chloride dihydrate in 50 ml of concentrated HCl and 25 ml of water. After one night, the expected product is obtained by filtration, rinsing with 1N HCl and with water, m=23.96 g.

Workup

  1. temperatureto maintain the temperature at 0° C
  2. customThe suspension thereby obtained
  3. temperaturecooled beforehand to 0° C.
  4. waitleft
  5. additionThe reaction mixture is added slowly to a solution
  6. waitAfter one night

Sources & evidence

ORD record
ord-44b64973a4d6423791beb8aa4ff8b6c6
Source dataset
uspto-grants-1996_06
Patent number
US05523455

Linked notes

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