Formamide → 4-chloroisoindole-1,3-dione

HRID 1659949Notes

Reaction equation

HRID 1659949 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:5]([NH:15][C:8](=[O:7])[C:3]=12)=[O:6]

Participants

4

Reactant 2

HCID 713FormamideHCID 670143-Chlorophthalic anhydride

Product 1

HCID 2312384-chloroisoindole-1,3-dioneYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

(b 1) 300 parts of 3-chlorophthalic anhydride in 1,200 parts by volume of formamide are stirred for 2 hours at 140° C. The mixture is then allowed to cool to 100° C. after which the solution is poured into 5,000 parts by volume of water. The precipitate which forms is filtered off, washed with water and dried under reduced pressure. 275 parts (92.2% of theory) of 3-chlorophthalimide, of melting point 236°-238° C., are obtained.

Workup

  1. filtrationThe precipitate which forms is filtered off
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-13844a440a624164881cb39fa99eb1bf
Source dataset
uspto-grants-1981_12
Patent number
US04306074

Reaction notes

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