Nitric Acid → HCID 22623284, compound

HRID 840360Notes

Reaction equation

HRID 840360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1.[N+:20]([O-])([OH:22])=[O:21]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:20]([O-:22])=[O:21])=[CH:6][C:5]([N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])=[C:4]([F:19])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 22623287HCID 22623287, compound

Product 1

HCID 22623284HCID 22623284, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of 49.6 g of N-(4-chloro-2-fluorophenyl)phthalimide and 180 ml of concentrated sulfuric acid was cooled in an ice bath, and a mixed acid consisting of 22.7 g of 60% nitric acid and 18 ml of concentrated sulfuric acid was slowly added dropwise under stirring (reaction temperature<10° C.). After the dropwise addition, the stirring was continued under cooling in an ice bath for 1 hour and then at room temperature for 1 hour. The reaction mixture was poured into ice-water, and the precipitated solid was collected by filtration. The resulting solid was washed successively with water and methanol and dried under reduced pressure to give 57.2 g of the title compound.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionwas slowly added dropwise
  3. custom(reaction temperature<10° C.)
  4. additionAfter the dropwise addition
  5. temperatureunder cooling in an ice bath for 1 hour
  6. filtrationthe precipitated solid was collected by filtration
  7. washThe resulting solid was washed successively with water and methanol
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-0f721977cbcd43f3a984b63b9b29c7e2
Source dataset
uspto-grants-2002_04
Patent number
US06365753B1

Reaction notes

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