Réaction #366160

Équation de réaction

fluoroboric acid

4-amino-1,8-naphthalic anhydride

sodium nitrite

→

title compound

Rendement 61.6%

4-Hydroxy-1,8-naphthalic anhydride

Rendement 61.6%

Solvants

water

sulfuric acid

water

sulfuric acid

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGwith stirring for 30 minutes
2. 2
   AutreThe precipitate was isolated
3. 3
   Températurerefluxed for 3 hours
4. 4
   workup.ADDITIONagain poured onto ice
5. 5
   AutreThe precipitate was isolated
6. 6
   Lavagewashed with water
7. 7
   Autredried

Mode opératoire

To a solution of 1.0 g (4.7 mmol) of 4-amino-1,8-naphthalic anhydride in 5 mL concentrated sulfuric acid at 0° C. to 5° C. was added 1.0 g (14.5 mmol) of sodium nitrite, and then 0.5 mL of water. The reaction was stirred for 30 minutes at 0° C. to 5° C., followed by addition of 5 mL (38 mmol) of 48% aqueous fluoroboric acid, with stirring for 30 minutes. The mixture was poured into ice water. The precipitate was isolated, suspended in a solution of 10 mL concentrated sulfuric acid in 50 mL water, refluxed for 3 hours, and again poured onto ice. The precipitate was isolated, washed with water, and dried to yield 620 mg of the title compound.

Source