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

HRID 278978

Reaction equation

HRID 278978 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 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.

Workup

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

Sources & evidence

ORD record
ord-8aecf3b11c6d4a569e58523b7a85b81b
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Linked notes

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