Anthranilic Acid → 3,5-Dichlorobenzoic acid

HRID 426928Notes

Reaction equation

HRID 426928 reaction equation
N[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[ClH:11].[Cl:12]Cl.N([O-])=O.[Na+]>O.C(O)(C)C>[Cl:11][C:10]1[CH:2]=[C:3]([CH:7]=[C:8]([Cl:12])[CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 24526ChlorineHCID 23668193Sodium Nitrite

Product 1

HCID 58113,5-Dichlorobenzoic acidYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

137 parts of 2-aminobenzoic acid are introduced into 2,000 parts of 10 percent strength by weight hydrochloric acid. 138 parts of chlorine gas are passed in at 30° C. over 3 hours. 800 parts of isopropanol are then added. A solution of 100 parts of sodium nitrite in 140 parts of water is introduced in the coarse of 6 hours at 85° C.; nitrogen is evolved. The mixture is cooled and the product is filtered off. 158 parts (83% of theory) of 3,5-dichlorobenzoic acid of melting point 176°-179° C. are obtained.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-c1d5e2a465b94489b8579ad65090e4b0
Source dataset
uspto-grants-1979_10
Patent number
US04172098

Reaction notes

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