Hydrochloric Acid → Benzoic acid, 2-amino-5-fluoro-3-nitro- (9CI)

HRID 1470593Notes

Reaction equation

HRID 1470593 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7]C(=O)[C:5]2=[O:15].[OH:16]O.Cl>[OH-].[Na+]>[NH2:7][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[C:5]([OH:15])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 167952125-Fluoro-7-nitroindole-2,3-dione

Product 1

HCID 18548624Benzoic acid, 2-amino-5-fluoro-3-nitro- (9CI)Yield 70.17%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a slurry of 5-fluoro-7-nitro-1H-indole-2,3-dione (3 g, 14.2 mmol) in aqueous 5N NaOH solution (30 mL) was added slowly an aq. solution of 33% hydrogen peroxide (3 mL) at 0° C. After completion of the addition, the reaction mixture was stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture was acidified with 2N HCl and the resulting precipitate was filtered, washed with water (2-3 times) and dried under vacuum to obtain the title compound as yellow solid (2 g, 70.17%).

Workup

  1. additionAfter completion of the addition
  2. customAfter completion of the reaction
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with water (2-3 times)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-de4a65c515fa47d1830b9e947c4ae8d3
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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