Formamide → 4-chloroisoindole-1,3-dione

HRID 2377595Notes

Reaction equation

HRID 2377595 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-68e803d483744342ad7283d5b46bb84e
Source dataset
uspto-grants-2008_12
Patent number
US07470664B2

Reaction notes

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