Anthranilic Acid → 5-Chloroisatoic anhydride

HRID 215793Notes

Reaction equation

HRID 215793 reaction equation
NC1C=CC=CC=1[C:4](O)=[O:5].[NH2:11][C:12]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[Cl:21][C:18]1[CH:17]=[C:13]2[C:14]([O:16][C:4](=[O:5])[NH:11][C:12]2=[CH:20][CH:19]=1)=[O:15]

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 124762-Amino-5-chlorobenzoic acidHCID 94429Triphosgene

Product 1

HCID 784805-Chloroisatoic anhydrideYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isatoic anhydrides were prepared from 2-aminobenzoic acid derivatives using the following procedure. A solution of 2-amino-5-chlorobenzoic acid (1.56 g, 9.7 mmol) in 25 mL of dry THF and triphosgene (1.00 g, 3.3 mmol) was stirred at room temperature for 18 h. The resultant solid was filtered, washed with cold acetone, and dried under vacuum to give 1.56 g (89%) of 5-chloroisatoic anhydride.

Workup

  1. filtrationThe resultant solid was filtered
  2. washwashed with cold acetone
  3. customdried under vacuum

Sources & evidence

ORD record
ord-33d43fc23d5f47c2a0646fa1bb768808
Source dataset
uspto-grants-2012_06
Patent number
US08193185B2

Reaction notes

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