Water → HCID 19425292, compound

HRID 742435Notes

Reaction equation

HRID 742435 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:5][C:3]=1[NH2:4].[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2[CH2:21][CH2:22][CH2:23][CH2:24][C:16]1=2.O>C(O)(=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:5][C:3]=1[N:4]1[C:18](=[O:19])[C:17]2[CH2:21][CH2:22][CH2:23][CH2:24][C:16]=2[C:15]1=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 19425230HCID 19425230, compound

Product 1

HCID 19425292HCID 19425292, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Fluoro-5-cyclopentyloxyaniline (330 mg, 1.69 mmol), 3,4,5,6-tetrahydrophthalic anhydride (258 mg, 1.70 mmol) and acetic acid (10 ml) as a solvent were placed in a round bottom flask (50 cc) followed by heating under refluxing for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate (20 ml×3 portions). The organic layers were combined, and, after washing with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate. After removing the drying agent, the solvent was distilled off under reduced pressure. The resulting dark red oily substance (345 mg) was isolated and purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) to obtain the derired N-(2-fluoro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide as a light yellow oily substance (171 mg, 0.575 mmol, 34% yield).

Workup

  1. temperatureby heating
  2. temperatureunder refluxing for 5 hours
  3. customAfter completion of the reaction
  4. extractionthe mixture was extracted with ethyl acetate (20 ml×3 portions)
  5. washafter washing with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  7. customAfter removing the drying agent
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting dark red oily substance (345 mg) was isolated
  10. custompurified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-f4032ef031b343c2945af31ee2f1f34d
Source dataset
uspto-grants-1996_09
Patent number
US05554581

Reaction notes

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