Formamide → 4-chloroisoindole-1,3-dione

HRID 1511536Notes

Reaction equation

HRID 1511536 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=O)[C:3]=12)=[O:6].C([NH2:15])=O>O>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:3]=1[C:8](=[O:7])[NH:15][C:5]2=[O:6]

Participants

4

Reactant 2

HCID 713FormamideHCID 670143-Chlorophthalic anhydride

Product 1

HCID 2312384-chloroisoindole-1,3-dioneYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 3-chlorophthalic acid anhydride (9 g, 49.2 mmol) and formamide (100 mL) was heated to 125° C. and stirred for 3 h. Water (300 mL) was then added and the mixture was cooled to room temperature. The mixture was filtered and the resulting white solid was washed with water and dried to give 4-chloro-1H-isoindole-1,3(2H)-dione (7.7 g, 86% yield).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. washthe resulting white solid was washed with water
  4. customdried

Sources & evidence

ORD record
ord-1f72a5a000e641f6b622ab01e30fdc42
Source dataset
uspto-grants-2012_07
Patent number
US08216999B2

Reaction notes

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