Water → 2-(2-Fluorobenzoyl)-1-phthalimidopyrrole

HRID 462738Notes

Reaction equation

HRID 462738 reaction equation
[C:1]1(=[O:16])[N:5]([N:6]2[CH:10]=[CH:9][CH:8]=[CH:7]2)[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12.[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].O>ClC(Cl)C>[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([C:7]1[N:6]([N:5]2[C:4](=[O:11])[C:3]3=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]3[C:1]2=[O:16])[CH:10]=[CH:9][CH:8]=1)=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 98082-Fluorobenzoyl chlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

Product 1

HCID 134577152-(2-Fluorobenzoyl)-1-phthalimidopyrroleYield 19.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of N-phthalimidopyrrole (10 g, 47 mmole) and fused zinc chloride (10 g, 73 mmole) in 80 ml dichloroethane was added o-fluorobenzoyl chloride (7.5 g, 47 mmole). The reaction mixture was stirred at ambient temperature for twenty hours and at 80° for one hour. Thereafter, it was cooled, poured into water and extracted with dichloromethane. The organic extract was washed with water and with saturated sodium chloride solution, and dried over magnesium sulfate. The solution was filtered and evaporated to an oil which yielded a solid upon trituration with ethanol (yield 11 g, m.p. 180°-190°). This material was purified by column chromatography (silica gel, dichloromethane) to give 3 g solid. This material was recrystallized from isopropanol to give 2.6 g (17%) crystals, m.p. 202°-203°.

Workup

  1. temperatureThereafter, it was cooled
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water and with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe solution was filtered
  7. customevaporated to an oil which
  8. customyielded a solid upon trituration with ethanol (yield 11 g, m.p. 180°-190°)
  9. customThis material was purified by column chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-42b46ed611a4422ca218c74334337054
Source dataset
uspto-grants-1985_05
Patent number
US04517195

Reaction notes

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