Oxalyl chloride → 5-Chloroisatoic anhydride

HRID 2110036Notes

Reaction equation

HRID 2110036 reaction equation
[C:1]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14](Cl)[C:10]=1[C:11]([OH:13])=[O:12])(OC(C)(C)C)=[O:2].C(Cl)(=O)C([Cl:22])=O>C1(C)C=CC=CC=1>[Cl:22][C:15]1[CH:14]=[C:10]2[C:11]([O:13][C:1](=[O:2])[NH:8][C:9]2=[CH:17][CH:16]=1)=[O:12]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 177504472-[(tert-Butoxycarbonyl)amino]-6-chlorobenzoic acid

Product 1

HCID 784805-Chloroisatoic anhydride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After suspending 2-(Boc)amino-6-chlorobenzoic acid (1.51 g, 5.56 mmol) in toluene (20 mL), the mixture was heated to reflux. Oxalyl chloride (0.572 mL, 6.67 mmol) was added dropwise thereto, and the mixture was vigorously stirred for 10 minutes. After cooling the reaction mixture on ice, the precipitated crystals were filtered out, washed with n-hexane and dried in a desiccator to obtain 5-chloroisatoic anhydride.

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureAfter cooling the reaction mixture on ice
  3. filtrationthe precipitated crystals were filtered out
  4. washwashed with n-hexane
  5. customdried in a desiccator

Sources & evidence

ORD record
ord-f70b25d3c94f4b0ea9b6af9c6d3fc4b9
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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