Reacción #742281

Ecuación de reacción

NaNO2

6-aminonaphthalene-2-sulfonic acid

NaOH

SnCl2

H2SO4

→

6-hydrazinylnaphthalene-2-sulfonic acid

Rendimiento 77.2%

Disolventes

H2O

HCl

H2O

H2O

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter the solution was stirred at 0° C. for 2 h
2. 2
   Otrothe diazonium salt was removed by filtration
3. 3
   Lavadowashed with cold water
4. 4
   workup.STIRRINGThe mixture was stirred overnight
5. 5
   FiltraciónThe solid was filtered
6. 6
   Lavadowashed twice with water
7. 7
   Otrodried under vacuum

Procedimiento

To a solution of 6-aminonaphthalene-2-sulfonic acid (2.23 g, 10 mmol) in 15 ml of H2O was added 2N NaOH (0.75 ml). The mixture was stirred for 5 min at RT and conc. H2SO4 (0.68 g, 6.9 mmol) was added to it dropwise at 0° C. 2 ml of iced H2O was added, followed by a solution of NaNO2 (1.04 g, 15 mmol) in 2 ml of H2O. After the solution was stirred at 0° C. for 2 h, the diazonium salt was removed by filtration and washed with cold water. The salt was then added in portions to a cold (<0° C.) solution of SnCl2 (4.9 g, 22 mmol) in 3.2 ml of conc. HCl and 1.8 ml of H2O. The mixture was stirred overnight. The solid was filtered and washed twice with water, dried under vacuum to give 1.84 g of 6-hydrazinylnaphthalene-2-sulfonic acid (77%), which was used directly for next step.

Fuente