Anthranilic Acid → Benzoic acid, 2-amino-5-iodo-

HRID 2225038Notes

Reaction equation

HRID 2225038 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I:11](O)(=O)=O>C(O)(=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 227Anthranilic AcidHCID 24345Iodic acid

Product 1

HCID 72911Benzoic acid, 2-amino-5-iodo-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 5.00 g (36.4 mmole) of 2-aminobenzoic acid, 100 ml of acetic acid and 3.56 g (14.0 mmole) of molecular iodine, 2.12 g (8.4 mmole) of a 70% by weight aqueous solution of iodic acid was added dropwise. After the reaction mixture was stirred at the room temperature for 3 hour, the reaction mixture was analyzed in accordance with the high performance liquid chromatography. The results of the reaction are shown in Table 1. It was shown by the values obtained by the analysis of the reaction mixture that the yield of 2-amino-5-iodobenzoic acid was 60% as calculated based on the amount of iodine atom (this result is shown in the parenthesis since this result is different from the yield of the isolated product). A relatively great conversion was obtained when iodic acid of the oxidizing agent was used as the iodinating agent. However, it was difficult that the selectivity of the object product as great as that obtained by using hydrogen peroxide was obtained.

Workup

  1. additionwas added dropwise
  2. customThe results of the reaction

Sources & evidence

ORD record
ord-8bccf2cac2c34dd39a7bce9685e0620f
Source dataset
uspto-grants-2008_05
Patent number
US07378546B2

Reaction notes

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