Potassium Iodide → 2-[2-nitro-4-(trifluoromethyl)phenyl]-1H-benz[de]isoquinoline-1,3(2H)-dione

HRID 1648811

Reaction equation

HRID 1648811 reaction equation
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([NH:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=[O:12])[CH:10]=1.Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[N+:27]([C:18]1[CH:19]=[C:20]([C:23]([F:24])([F:25])[F:26])[CH:21]=[CH:22][C:17]=1[N:13]1[C:14](=[O:15])[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]3[C:8]=2[C:9](=[CH:10][CH:1]=[CH:2]3)[C:11]1=[O:12])([O-:29])=[O:28]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 66491Naphthalimide

Product 1

HCID 201990122-[2-nitro-4-(trifluoromethyl)phenyl]-1H-benz[de]isoquinoline-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Eight-tenths mole (157.6 g.) of 1,8-naphthalimide, 260 g. (1.15 m.) of 4-chloro-3-nitrobenzotrifluoride, 64 g. (0.46 m.) of anhydrous potassium carbonate, about 4 g. (0.024 m.) of potassium iodide, and 2400 ml. of dry N,N-dimethylformamide were allowed to reflux under a nitrogen atmosphere for about 8 hours. The reaction mixture was allowed to cool to room temperature and the reaction vessel was then chilled in an ice-bath. The resulting precipitate was filtered, washed with water, and dried in vacuo to yield crude 2-[2-nitro-4-(trifluoromethyl)phenyl]-1H-benz[de]isoquinoline-1,3-(2H)-dione.

Workup

  1. temperatureto reflux under a nitrogen atmosphere for about 8 hours
  2. temperaturethe reaction vessel was then chilled in an ice-bath
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d85c861f023041b69af1741ee9e2a33f
Source dataset
uspto-grants-1983_11
Patent number
US04413126

Linked notes

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