Hydrochloric Acid → 2-Amino-4-chloro-6-nitrobenzoic acid

HRID 1781635Notes

Reaction equation

HRID 1781635 reaction equation
[OH:1]O.[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8](=[O:14])C(=O)[NH:10]2)=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=1.Cl>[OH-].[Na+]>[Cl:3][C:4]1[CH:12]=[C:11]([NH2:10])[C:7](=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=1)[C:8]([OH:14])=[O:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 19046765HCID 19046765, compound

Product 1

HCID 190467352-Amino-4-chloro-6-nitrobenzoic acidYield 87.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4 ml of a 30% hydrogen peroxide solution are added dropwise at room temperature to 3.8 g (16.7 mmol) of 6-chloro-4-nitro-indoline-2,3-dione in 60 ml of sodium hydroxide solution. The mixture is stirred for 2 hours at room temperature, acidified to pH 2 to 3 with 4N hydro-chloric acid, filtered and dried. 3.18 g (87.8% of theory) of 4-chloro-6-nitro-anthranilic acid having a melting point of 202°-205° are obtained.

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-03f44ecdfc44402a90066612773e8a0e
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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