Anthranilic Acid → 5-Chloroisatoic anhydride

HRID 1756562Notes

Reaction equation

HRID 1756562 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-941f11ef93b7496a842f854e69a19bde
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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