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Dichloromethane → 2-(3-Chloro-2,5,6-trifluoropyridin-4-yl)-1H-isoindole-1,3(2H)-dione

HRID 1274721
Notes
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Reaction equation

HRID 1274721 reaction equation
ClCCl.[Cl:4][C:5]1[C:6]([F:14])=[N:7][C:8]([F:13])=[C:9]([F:12])[C:10]=1F.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K]>C(Cl)(Cl)Cl>[Cl:4][C:5]1[C:6]([F:14])=[N:7][C:8]([F:13])=[C:9]([F:12])[C:10]=1[N:19]1[C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]2[C:15]1=[O:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 1371833-Chloro-2,4,5,6-tetrafluoropyridineHCID 24194345Phthalimide potassium salt

Product 1

HCID 221212012-(3-Chloro-2,5,6-trifluoropyridin-4-yl)-1H-isoindole-1,3(2H)-dioneYield 102.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a mixed solution of 40 ml dichloromethane and 20 ml N,N-methylformamide were added 18.5 g of 3-chloro-2,4,5,6-tetrafluoropyridine and 20.5 g potassium phthalimide, and the mixture was stirred at 40° C. for one day. After adding 40 ml of chloroform, the mixture was washed twice with 500 ml of distilled water and once with 500 ml of 0.5% aqueous solution of sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The precipitate was dispersed in diisopropylether, and collected by filtration to obtain 32.0 g of the title compound as a colorless powder.

Workup

  1. washthe mixture was washed twice with 500 ml of distilled water and once with 500 ml of 0.5% aqueous solution of sodium hydroxide
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionThe precipitate was dispersed in diisopropylether
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f515df2394f34b938f3b61ccbfa8d63d
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06156903

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes