Hydrochloric Acid → 2-Amino-5-chloro-3-nitrobenzoic acid

HRID 1470621Notes

Reaction equation

HRID 1470621 reaction equation
[Cl: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]([Cl:1])=[CH:3][C:4]=1[C:5]([OH:15])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 149531845-chloro-7-nitro-1H-indole-2,3-dione

Product 1

HCID 2320552-Amino-5-chloro-3-nitrobenzoic acidYield 70.17%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a slurry of 5-chloro-7-nitro-1H-indole-2,3-dione (3.2 g, 14.15 mmol) in aqueous 5N NaOH solution (30 mL) added an aq. solution of 33% hydrogen peroxide solution (3 mL) slowly at 0° C. After the addition, the reaction mixture was stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture was acidified with an aq. solution of 2N HCl and the resulting precipitated 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 the addition
  2. customAfter completion of the reaction
  3. customthe resulting precipitated
  4. filtrationwas filtered
  5. washwashed with water (2-3 times)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-17bc456ebff54418a5f6963bfbb23c5b
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

Loading…