Tetrafluoroboric acid → 4-Hydroxy-1,8-naphthalenedicarboxylic anhydride

HRID 566989

Reaction equation

HRID 566989 reaction equation
[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[C:4](N)[CH:5]=[CH:6]3)[CH:2]=1)=[O:12].N([O-])=[O:18].[Na+].F[B-](F)(F)F.[H+]>S(=O)(=O)(O)O.O>[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[C:4]([OH:18])[CH:5]=[CH:6]3)[CH:2]=1)=[O:12]

Participants

6

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 809904-Aminonaphthalene-1,8-dicarboxylic anhydrideHCID 23668193Sodium Nitrite

Product 1

HCID 59994974-Hydroxy-1,8-naphthalenedicarboxylic anhydrideYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent2×

Procedure

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 in 3 hours, and again poured onto ice. The precipitate was isolated, washed with water, and dried to yield 620 mg of the title compound.

Workup

  1. stirringwith stirring for 30 minutes
  2. customThe precipitate was isolated
  3. temperaturerefluxed in 3 hours
  4. additionagain poured onto ice
  5. customThe precipitate was isolated
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-56d8348d4c064626a6e1348ebb805143
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Linked notes

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