Ethyl chloroformate → 5-Methylisatoic anhydride

HRID 1910201Notes

Reaction equation

HRID 1910201 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13](OCC)=[O:14]>C(Cl)(=O)C>[CH3:11][C:8]1[CH:7]=[C:3]2[C:4]([O:6][C:13](=[O:14])[NH:1][C:2]2=[CH:10][CH:9]=1)=[O:5]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 2944785-Methylisatoic anhydrideYield 80%

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

15.1 g (100 mmol) of 2-amino-5-methyl-benzoic acid was refluxed with 60 mL of ethyl chloroformate for 6 h, and then was refluxed for another 3 h after addition of 60 mL of acetyl chloride. The solid was collected, washed with hexane to give 14.2 g (80%) of the 5-methylisatoic anhydride.

Workup

  1. temperaturewas refluxed for another 3 h
  2. customThe solid was collected
  3. washwashed with hexane

Sources & evidence

ORD record
ord-6458972b70a04a0ea1303cf1dad47ad1
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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