Water → 4-Chloroisatoic anhydride

HRID 1602590Notes

Reaction equation

HRID 1602590 reaction equation
[C:1]1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]([NH2:18])[C:12](=[CH:16][CH:17]=1)[C:13]([OH:15])=[O:14].[OH2:19]>[Cl-].C([N+]1C=CC=CC=1)CCCCCCCCCCC>[CH:17]1[C:9]([Cl:8])=[CH:10][C:11]2[NH:18][C:1]([O:14][C:13](=[O:15])[C:12]=2[CH:16]=1)=[O:19]

Participants

5

Reactant 3

HCID 962Water2×HCID 1140TolueneHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 3291054-Chloroisatoic anhydrideYield 101.7%

Reagents, catalysts & solvents 1

HCID 7717Dodecylpyridinium chlorideCatalyst

Conditions

Temperature
20 °C

Procedure

According to the same manner as in Example 3, except that the flask was changed to 500 ml flask, 70 g of water, 280 g of toluene and 35 g of 4-chloroanthranilic acid were in place of 53 g of water and 2.8 g of laurylpyridinium chloride, and that the reaction temperature was maintained at 15-25° C., 41.0 g of 7-chloroisatoic anhydride (purity: 94%) was obtained.

Workup

  1. customwas changed to 500 ml flask

Sources & evidence

ORD record
ord-c5f130b027004225ac950ec4ee205d4e
Source dataset
uspto-grants-1999_11
Patent number
US05981749

Reaction notes

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